Active compound combinations comprising phenylamidine compounds and further fungicides

ABSTRACT

The present invention relates to novel fungicidal active compound combinations or compositions comprising a phenylamidine compound of formula (I) and further active compounds (II) and (III) selected from the groups (A), (B) and/or (C), to a process for preparing these active compound combinations or compositions and to the use thereof as biologically active compound combinations or compositions, especially for the control of phytopathogenic fungi in plants and/or in the protection of materials and/or as plant growth regulators.

CROSS REFERENCE TO RELATED APPLICATIONS

This application is a §371 National State Application ofPCT/EP2015/052710, filed Feb. 10, 2015, which claims priority toEuropean Application No. 14154956.8 filed Feb. 13, 2014.

BACKGROUND

Field of Invention

The present invention relates to novel fungicidal active compoundcombinations comprising a phenylamidine compound of formula (I) andfurther active compounds (II) and (III), selected from the groups (A),(B) and/or (C) to a process for preparing these active compoundcombinations and to the use thereof as biologically active compoundcombinations or crop protection compositions, especially for the controlof phytopathogenic fungi in plants and/or in the protection of materialsand/or as plant growth regulators.

Description of Related Art

WO-A 00/46 184 and WO-A 08/110313 each disclose the use ofphenylamidines as fungicides and their preparation starting fromcommercially available materials. WO-A 08/110313 disclosesphenoxyphenyl-amidine compounds according to formula (I), methods forproducing such compounds starting from commercially availableingredients and their fungicidal uses.

WO-A 03/024 219, WO-A 05/089 547 and WO-A 05/120 234 generally disclosefungicide compositions comprising at least one phenylamidine and atleast one further known fungicidally active ingredient. Object of theseearlier inventions are mainly binary compositions referring inter aliato the binary combination of phenylamidines and further fungicides.Further it is generally stated therein, that such binary compositionsmay further comprise additional components such as fungicides but noconcrete ternary combinations are specified.

Since the environmental and economic requirements imposed on modern-daycrop protection compositions are continually increasing, with regard,for example, to the spectrum of action, toxicity, selectivity,application rate, formation of residues, and favourable preparationability, and since, furthermore, there may be problems, for example,with resistances, a constant task is to develop new, alternative cropprotection compositions, in particular fungicidal crop protectioncompositions, which in some areas at least help to fulfil theabovementioned requirements. One way of fulfilling such need can be thedevelopment of novel compositions comprising several fungicides whichhave advantages over the known compositions at least in some areas.

In view of this, it was in particular an object of the present inventionto provide active compound combinations or compositions which exhibitfungicidal activity against phytopathogenic fungi in plants, in theprotection of materials and as plant growth regulators. Moreover, it wasa further particular object of the present invention, to reduce theapplication rates and broaden the activity spectrum of the fungicides,and thereby to provide an active compound combination or compositionwhich, preferably at a reduced total amount of active compounds applied,has improved fungicidal activity against phytopathogenic fungi.

The present invention provides active compound combinations orcompositions which in some aspects at least achieve the statedobjective, i.e. which exhibit fungicidal activity againstphytopathogenic fungi in plants and/or in the protection of materialsand/or as plant growth regulators. Moreover it has been found,surprisingly, that the active compound combinations according to theinvention not only bring about the additive enhancement of the spectrumof action with respect to the phytopathogenic fungi to be controlledthat was in principle to be expected but achieves a synergistic effectwhich extends the range of action of the component (I) and of thecomponents (II) and (III) in two ways. Firstly, the rates of applicationof the component according to formula (I) and of the components (II) and(III) are lowered whilst the action remains equally good. Secondly, theactive compound combination still achieves a high degree of control ofphytopathogenic fungi in plants even where the three individualcompounds have become totally ineffective in such a low application raterange. This allows, on the one hand, a substantial broadening of thespectrum of phytopathogenic fungi that can be controlled and, on theother hand, increased safety in use.

In addition to the fungicidal synergistic activity, the active compoundcombinations according to the invention have further surprisingproperties which, in a wider sense, may also be called synergistic, suchas, for example: broadening of the fungicidal activity spectrum toresistant strains of plant diseases, such as fungicide resistantphytopathogenic fungi; lower application rates of the active compoundcombinations; sufficient control of phytopathogenic fungi with the aidof the active compound combinations according to the invention even atapplication rates where the individual compounds show no or virtually noactivity; advantageous behaviour during formulation or during use;improved storage stability and light stability; advantageous residueformation; improved toxicological or ecotoxicological behaviour;improved properties of the plant so called plant physiology effects, forexample better growth, increased harvest yields, a better developed rootsystem, a larger leaf area, greener leaves, stronger shoots, less seedrequired, lower phytotoxicity, mobilization of the defence system of theplant, good compatibility with plants. Thus, the use of the activecompound combinations or compositions according to the inventioncontributes considerably to keeping young plants stand healthy, which,for example, safeguards quality and yield. Moreover, the active compoundcombinations according to the invention may contribute to enhancedsystemic action. Even if the individual compounds of the active compoundcombination have no sufficient systemic properties, the active compoundcombinations according to the invention may have this property. In asimilar manner, the active compound combinations according to theinvention may result in higher long term efficacy of the fungicidalaction.

SUMMARY OF THE INVENTION

It has surprisingly been found that active compound combinationscomprising

-   -   (1) at least one compound of the formula (I)

-   -   in which        -   R¹ is selected from the group consisting of methyl and            ethyl;        -   R² is selected from the group consisting of a Cl atom and a            methyl group;        -   R³ is selected from the group consisting of a Cl-atom and a            methyl group;        -   R⁴ is selected from the group consisting of hydrogen,            halogen or methyl;        -   R⁵ is selected from the group consisting of hydrogen,            halogen or methyl;    -   and salts, N-oxides, metal complexes or stereoisomers thereof    -   and    -   (2) at least two compounds (II) and (III) selected from the        groups (A), (B) and/or (C):        -   (A) the group of inhibitors of the ergosterol biosynthesis;        -   (B) the group of inhibitors of the respiratory chain at            complex I or II; and        -   (C) the group of inhibitors of the respiratory chain at            complex III;    -   with the proviso that the specified compounds (II) and (III) are        not identical;        act in a fungicidal fashion. Accordingly, the present invention        is directed to ternary active compound combinations of compounds        of the formula (I) and compounds (II) and (III) selected from        the groups (A), (B) and/or (C). In some embodiments, such active        compound combinations or compositions act in a synergistic        fashion.

In case a compound of the group (A) is used in combination with thecompound of the formula (I) and a further active compound, the compound(A) of the group of inhibitors of the ergosterol biosynthesis isselected from the group consisting of (A.1) cyproconazole (113096-99-4),(A.2) epoxiconazole (106325-08-0), (A.3) prothioconazole (178928-70-6)and/or (A.4) tebuconazole (107534-96-3).

In case a compound of the group (B) is used in combination with thecompound of the formula (I) and a further active compound, the compound(B) of the group of inhibitors of the respiratory chain at complex I orII is selected from the group consisting of (B.1) bixafen (581809-46-3),(B.2) fluopyram (658066-35-4), (B.3) fluxapyroxad (907204-31-3), (B.4)isopyrazam (mixture of syn-epimeric racemate 1RS,4SR,9RS andanti-epimeric racemate 1RS,4SR,9SR) (881685-58-1), (B.5) penthiopyrad(183675-82-3), (B.6) benzovindiflupyr (1072957-71-1), (B.7) isofetamid(875915-78-9), (B.8)N-(5-chloro-2-isopropylbenzyl)-N-cyclopropyl-3-(difluoromethyl)-5-fluoro-1-methyl-1H-pyrazole-4-carboxamideand/or (B.9)3-(difluoromethyl)-N-methoxy-1-methyl-N-[1-(2,4,6-trichlorophenyl)propan-2-yl]-1H-pyrazole-4-carboxamide.

In case a compound of the group (C) is used in combination with thecompound of the formula (I) and a further active compound, the compound(C) of the group of inhibitors of the respiratory chain at complex IIIis selected from the group consisting of (C.1) azoxystrobin(131860-33-8), (C.2) picoxystrobin (117428-22-5), (C.3) pyraclostrobin(175013-18-0) and/or (C.4) trifloxystrobin (141517-21-7).

The invention also comprises a composition comprising an active compoundcombination according to the invention. Such a composition can furthercomprise at least one agriculturally suitable additive. The inventionalso comprises a method for preparing compositions comprising adding atleast one agriculturally suitable additive to the active compoundcombination according to the invention. Furthermore the inventioncomprises a method for reducing damage of plants and plant parts orlosses in harvested fruits or vegetables caused by phytopathogenic fungiby controlling such phytopathogenic fungi, comprising applying theactive compound combination or the crop protection composition to theplant or the phytopathogenic fungi or the habitat of the plant or thehabitat of the phytopathogenic fungi. Furthermore the inventionencompasses a method for curatively or preventively controllingphytopathogenic fungi comprising the use of an active compoundcombination or a composition for control of soybean diseases.Furthermore the invention encompasses a method for curatively orpreventively controlling phytopathogenic fungi comprising the use of anactive compound combination or a composition for control of cerealdiseases. The invention also encompasses the use of the active compoundcombination or the crop protection composition for reducing damage ofplants and plant parts or losses in harvested fruits or vegetablescaused by phytopathogenic fungi by controlling such phytopathogenicfungi. In this connection the plants can be genetically modified ornon-genetically modified. Furthermore the invention comprises the use ofactive compound combinations or compositions according to the inventionfor the treatment of seed, comprising contacting said seeds with theactive compound combinations or compositions. Finally, the presentinvention also relates to seed treated with the above-mentioned activecompound combination or crop protection composition.

In view of this, the problem underlying the present invention has beensolved by providing novel active compound combinations or cropprotection compositions which exhibit synergistic fungicidal activityagainst phytopathogenic fungi in plants. Moreover, the novel activecompound combinations or crop protection compositions according to theinvention enable reduced application rates and/or broaden the activityspectrum of the fungicides. Finally the novel active compoundcombinations or crop protection compositions provide improved fungicidalactivity against phytopathogenic fungi and consequently provideefficient disease control for reducing damage of plants and plant partsor losses in harvested fruits or vegetables.

DETAILED DESCRIPTION OF A PREFERRED EMBODIMENT

The present invention provides active compound combinations comprisingat least one compound of the formula (I) and at least two further activecompounds (II) and (III) as outlined above. Accordingly, the presentinvention is directed to ternary active compound combinations of thecompounds of the formula (I) and compounds (II) and (III).

According to the invention the term “active compound combination” shallmean a physical mixture comprising compounds of the formula (I) andcompounds (II) and (III) selected from the groups (A), (B) and/or (C).In the context of the present invention the expression “active compoundcombination” stands for the various combinations of compounds (I), (II)and (III), for example in a single “ready-mix” form, in a combined spraymixture composed from separate formulations of the single activecompounds, such as a “tank-mix”, and in a combined use of the singleactive ingredients when applied in a sequential manner, i.e. one afterthe other with a reasonably short period, such as a few hours or days.Preferably the order of applying the compounds (I), (II) and (III) isnot essential for working the present invention. According to theinvention the term “composition” means a combination of the activecompound combination with further agriculturally suitable additives,such as agriculturally suitable auxiliaries, e.g. solvents, carriers,surfactants, extenders or the like which are described later. The term“composition” also comprises the terms “crop protection composition” and“formulation”.

In general “pesticides” as well as the terms “pesticidal” and “acting ina pesticidal fashion” means the ability of a substance to exhibitactivity against harmful microorganisms and plant pests e.g. increasemortality or inhibit the growth rate of harmful microorganisms and/orplant pests. According to the present invention the term “harmfulmicroorganisms” includes phytopathogenic fungi and bacteria, in apreferred embodiment it refers to phytopathogenic fungi. Furthermore inthe sense of the present invention the term “plant pests” includeinsects and/or nematodes.

“Fungicides” as well as the terms “fungicidal”, “fungicidal activity”and “acting in a fungicidal fashion” refer to the ability of a substanceto increase mortality or inhibit growth rates of phytopathogenic fungi.Fungicides can be used in crop protection for control of phytopathogenicfungi. They are characterized by an outstanding efficacy against a broadspectrum of phytopathogenic fungi. As used herein, the term“phytopathogenic fungi” comprises all organisms of the kingdom of fungiincluding Oomycetes, which can cause damage of plants and/or damage ofplant parts and/or losses in harvested fruits or vegetables. Specificphytopathogenic fungi are described later.

“Insecticides” as well as the term “insecticidal” refers to the abilityof a substance to increase mortality or inhibit growth rate of insects.As used herein, the term “insects” comprises all organisms in the class“Insecta”.

“Nematicide” and “nematicidal” refers to the ability of a substance toincrease mortality or inhibit the growth rate of nematodes. In general,the term “nematode” comprises eggs, larvae, juvenile and mature forms ofsaid organism.

In the context of the present invention the term “damage of plants” or“damage of plant parts” comprises in comparison to uninfected orunharmed plants e.g. the decrease of plant growth or yield or thedecrease of plant vigor, comprising decrease of plant health, plantquality and seed vigor, a decreased resistance to harmful microorganismssuch as phytopathogenic fungi, a decreased abiotic stress tolerance,comprising decreased temperature tolerance, decreases drought toleranceand decreased recovery after drought stress, decreased water useefficiency (correlating to reduced water consumption), decreases floodtolerance, decreased ozone stress and UV tolerance, decreased tolerancetowards chemicals like heavy metals, salts, pesticides (safener) or thelike, an increased stand failure, decreased recovery, impaired greeningeffect and decreased photosynthetic efficiency. In particular suchdamages of plants or damage of plant parts are caused by phytopathogenicfungi.

Reducing the damage of plants and plant parts often results in healthierplants and/or in an increase in plant vigor and yield. The activecompound combinations and/or compositions according to the invention, incombination with good plant tolerance and favourable toxicity towarm-blooded animals and being tolerated well by the environment, aresuitable for protecting plants and plant parts, for increasing harvestyields and for improving the quality of the harvested material.

In the context of the present invention, “control of harmfulmicroorganisms” or “control of phytopathogenic fungi” means a reductionin infestation by harmful microorganisms, especially of phytopathogenicfungi, compared with the untreated plant measured as pesticidalefficacy, preferably a reduction by 25-50%, compared with the untreatedplant (100%), more preferably a reduction by 40-79%, compared with theuntreated plant (100%); even more preferably, the infection by harmfulmicroorganisms especially of phytopathogenic fungi is entirelysuppressed (by 70-100%). In a specific embodiment the active compoundcombinations and/or compositions according to the invention can be usedfor curative (i.e. for treatment of already infected plants) orprotective or preventive (i.e. for treatment of plants which have notyet been infected) control of phytopathogenic fungi. The inventiontherefore also relates to curative and protective methods forcontrolling phytopathogenic fungi by the use of the inventive activecompound combinations and/or compositions. The active compoundcombinations and/or compositions according to the invention are activeagainst normally sensitive and resistant species of phytopathogenicfungi and against all or some stages of development. The term“preventive control of phytopathogenic fungi” comprises the use ofactive compound combinations and/or compositions according to theinvention for the prevention of plant diseases. Thus, a further aspectof the present invention is the use of active compound combinationsand/or compositions according to the invention for controllingphytopathogenic fungi, e.g., in agriculture, in horticulture, inforests, in gardens and leisure facilities as well as in the protectionof stored products and materials.

The term “applying the composition to the plant or the phytopathogenicfungi or the habitat of the plant or the habitat of the phytopathogenicfungi” refers to the treatment of a plant and/or phytopathogenic fungiand/or the habitat of the plant or the phytopathogenic fungi with thecompositions according to the invention. The term “habitat of the plant”comprises the environment where the plant is growing, e.g. the soil ornutrition medium—which is in a radius of at least 30 cm, 20 cm, 10 cmaround the caulis or bole of a plant to be treated or which is at least30 cm, 20 cm, 10 cm around the root system of said plant to be treated,respectively. The term “habitat of the phytopathogenic fungi” as usedherein is defined as the seed, the plant or plant parts or the fruit. Italso comprises the soil or the nutrition medium in which the plantgrows—which is in a radius of at least 30 cm, 20 cm, 10 cm around thecaulis or bole of a plant to be treated or which is at least 30 cm, 20cm, 10 cm around the root system of said plant to be treated,respectively.

As used herein, the term “comprising” is to be interpreted as specifyingthe presence of the stated features, integers, steps, components orcompounds as referred to, but does not preclude the presence or additionof one or more features, integers, steps, components or compounds, orgroups thereof. Thus, e.g. an active compound combination or compositioncomprising a compound of the formula (I) and at least compounds (II) and(III) selected from the groups (A), (B) and/or (C) may comprise morecompounds than the actually cited ones, i.e. the active compoundcombination or composition may further comprise at least one furtherfeature, integer, step, component or compound, or groups thereof.However, in context with the present invention, the term “comprising”also encloses “consisting of” and “including”.

As used herein the term “at least one” shall refer to either onecompound, feature, integer, step, component or compound, but alsoencompasses the presence of (at least) two, (at least) three or (atleast) four features, integers, steps, components or compounds, orgroups thereof.

In the following preferred active compound combinations comprisingcompounds of the general formula (I) and compounds selected from thegroups (A), (B) and/or (C) are described.

In a first preferred embodiment of the present invention, the compoundof the general formula (I) is combined with at least one member of (A)the group of inhibitors of the ergosterol biosynthesis and at least onemember of (B) the group of inhibitors of the respiratory chain atcomplex I or II.

In a second preferred embodiment of the present invention, the compoundof the general formula (I) is combined with at least one member of (A)the group of inhibitors of the ergosterol biosynthesis and at least onemember of (C) the group of inhibitors of the respiratory chain atcomplex III.

In a third preferred embodiment of the present invention, the compoundof the general formula (I) is combined with at least one member of (B)the group of inhibitors of the respiratory chain at complex I or II andat least one member of (C) the group of inhibitors of the respiratorychain at complex III.

In a fourth preferred embodiment of the present invention, the compoundof the general formula (I) is combined with at least two members of (A)the group of inhibitors of the ergosterol biosynthesis.

In a fifth preferred embodiment of the present invention, the compoundof the general formula (I) is combined with at least two members of (B)the group of inhibitors of the respiratory chain at complex I or II.

In a sixth preferred embodiment of the present invention, the compoundof the general formula (I) is combined with at least two members of (C)the group of inhibitors of the respiratory chain at complex III.

Preferred active compound combinations are the following combinationsselected from the group consisting of: (I)+(B.1)+(A.3); (I)+(B.2)+(A.3);(I)+(B.6)+(A.3); (I)+(C.4)+(A.3); (I)+(C.1)+(A.3); (I)+(B.8)+(A.3);(I)+(B.1)+(A.4); (I)+(C.4)+(A.4); (I)+(B.8)+(A.4); (I)+(C.4)+(B.1);(I)+(C.1)+(B.6); (I)+(C.2)+(B.5); (I)+(C.2)+(B.6); (I)+(C.3)+(B.3);(I)+(B.8)+(C.4); (I)+(B.2)+(A.4); (I)+(C.4)+(A.1); (I)+(B.7)+(A.3);(I)+(B.7)+(A.4); (I)+(C.4)+(A.1); (I)+(B.2)+(B.1); (I)+(C.4)+(B.2);(I)+(B.7)+(B.1); (I)+(B.7)+(C.4); (I)+(B.6)+(A.4); (I)+(B.6)+(A.1);(I)+(B.6)+(A.2); (I)+(B.5)+(A.1); (I)+(B.5)+(A.2); (I)+(B.3)+(A.3);(I)+(B.3)+(A.4); (I)+(B.3)+(A.2); (I)+(B.4)+(A.1); (I)+(B.4)+(A.2);(I)+(C.4)+(B.6); (I)+(C.4)+(B.3); (I)+(C.1)+(A.4); (I)+(C.1)+(A.1);(I)+(C.1)+(A.2); (I)+(C.1)+(B.1); (I)+(C.1)+(B.3); (I)+(C.1)+(B.4);(I)+(C.3)+(A.3); (I)+(C.3)+(A.4); (I)+(C.3)+(A.2); (I)+(C.3)+(B.1);(I)+(C.2)+(A.3); (I)+(C.2)+(A.4); (I)+(B.8)+(C.1); (I)+(B.8)+(C.3);(I)+(B.9)+(A.4); (I)+(B.9)+(B.1) and (I)+(B.9)+(B.6).

Particularly preferred active compound combinations are the followingcombinations selected from the group consisting of: (I)+(B.6)+(A.4);(I)+(B.6)+(A.1); (I)+(B.6)+(A.2); (I)+(B.5)+(A.1); (I)+(B.5)+(A.2);(I)+(B.3)+(A.3); (I)+(B.3)+(A.4); (I)+(B.3)+(A.2); (I)+(B.4)+(A.1);(I)+(B.4)+(A.2); (I)+(C.4)+(B.6); (I)+(C.4)+(B.3); (I)+(C.1)+(A.4);(I)+(C.1)+(A.1); (I)+(C.1)+(A.2); (I)+(C.1)+(B.1); (I)+(C.1)+(B.3);(I)+(C.1)+(B.4); (I)+(C.3)+(A.3); (I)+(C.3)+(A.4); (I)+(C.3)+(A.2);(I)+(C.3)+(B.1); (I)+(C.2)+(A.3); (I)+(C.2)+(A.4); (I)+(B.8)+(C.1);(I)+(B.8)+(C.3); (I)+(B.9)+(A.4); (I)+(B.9)+(B.1) and (I)+(B.9)+(B.6).

More preferred active compound combinations are the followingcombinations selected from the group consisting of: (I)+(B.2)+(A.4);(I)+(C.4)+(A.1); (I)+(B.7)+(A.3); (I)+(B.7)+(A.4); (I)+(C.4)+(A.1);(I)+(B.2)+(B.1); (I)+(C.4)+(B.2); (I)+(B.7)+(B.1) and (I)+(B.7)+(C.4).

Most preferred active compound combinations are the followingcombinations selected from the group consisting of: (I)+(B.1)+(A.3);(I)+(B.2)+(A.3); (I)+(B.6)+(A.3); (I)+(C.4)+(A.3); (I)+(C.1)+(A.3);(I)+(B.8)+(A.3); (I)+(B.1)+(A.4); (I)+(C.4)+(A.4); (I)+(B.8)+(A.4);(I)+(C.4)+(B.1); (I)+(C.1)+(B.6); (I)+(C.2)+(B.5); (I)+(C.2)+(B.6);(I)+(C.3)+(B.3) and (I)+(B.8)+(C.4).

In a preferred embodiment of the present invention the active compoundcombinations comprise compounds of the formula (I) wherein thephenylamidine derivatives are represented by the following formula(I-a):

in which

-   -   R¹ is selected from the group consisting of methyl and ethyl;    -   R⁴ is selected from the group consisting of hydrogen, bromine,        chlorine, fluorine or methyl;        and salts, N-oxides, metal complexes or stereoisomers thereof        and at least two compounds (II) and (III) selected from the        group consisting of (A), (B) and/or (C) as mentioned above with        the proviso that the specified compounds (II) and (III) are not        identical.

In a particularly preferred embodiment of the present invention theactive compound combinations comprise compounds of the formula (I)wherein the phenylamidine derivatives are represented by the followingformula (I-b):

in which

-   -   R¹ is selected from the group consisting of methyl and ethyl;    -   R⁴ is selected from the group consisting of hydrogen, fluorine        or chlorine;        and salts, N-oxides, metal complexes or stereoisomers thereof        and at least two compounds (II) and (III) selected from the        group consisting of (A), (B) and/or (C) as mentioned above with        the proviso that the specified compounds (II) and (III) are not        identical.

In a more preferred embodiment of the present invention the activecompound combinations comprise compounds of the formula (I) wherein thephenylamidine derivatives are represented by the following formula(I-c):

in which

-   -   R¹ is selected from the group consisting of methyl and ethyl;        and salts, N-oxides, metal complexes or stereoisomers thereof        and at least two compounds (II) and (III) selected from the        group consisting of (A), (B) and/or (C) as mentioned above with        the proviso that the specified compounds (II) and (III) are not        identical.

In a most preferred embodiment of the present invention the activecompound combinations comprise compounds of the formula (I) wherein thephenylamidine derivatives are represented by the following formula(I-d):

and salts, N-oxides, metal complexes or stereoisomers thereof and atleast two compounds (II) and (III) selected from the group consisting of(A), (B) and/or (C) as mentioned above with the proviso that thespecified compounds (II) and (III) are not identical.

In the following active compound combinations comprising compounds ofthe general formula (I-a) and compounds selected from the groupconsisting of (A), (B) and/or (C) are described.

In a first embodiment of the present invention, the compound of thegeneral formula (I-a) is combined with at least one member of (A) thegroup of inhibitors of the ergosterol biosynthesis and at least onemember of (B) the group of inhibitors of the respiratory chain atcomplex I or II.

In a second embodiment of the present invention, the compound of thegeneral formula (I-a) is combined with at least one member of (A) thegroup of inhibitors of the ergosterol biosynthesis and at least onemember of (C) the group of inhibitors of the respiratory chain atcomplex III.

In a third embodiment of the present invention, the compound of thegeneral formula (I-a) is combined with at least one member of (B) thegroup of inhibitors of the respiratory chain at complex I or II and atleast one member of (C) the group of inhibitors of the respiratory chainat complex III.

In a fourth embodiment of the present invention, the compound of thegeneral formula (I-a) is combined with at least two distinct members of(A) the group of inhibitors of the ergosterol biosynthesis.

In a fifth embodiment of the present invention, the compound of thegeneral formula (I-a) is combined with at least two distinct members of(B) the group of inhibitors of the respiratory chain at complex I or II.

In a sixth embodiment of the present invention, the compound of thegeneral formula (I-a) is combined with at least two distinct members of(C) the group of inhibitors of the respiratory chain at complex III.

Preferred active compound combinations are the following combinationsselected from the group consisting of: (I-a)+(B.1)+(A.3);(I-a)+(B.2)+(A.3); (I-a)+(B.6)+(A.3); (I-a)+(C.4)+(A.3);(I-a)+(C.1)+(A.3); (I-a)+(B.8)+(A.3); (I-a)+(B.1)+(A.4);(I-a)+(C.4)+(A.4); (I-a)+(B.8)+(A.4); (I-a)+(C.4)+(B.1);(I-a)+(C.1)+(B.6); (I-a)+(C.2)+(B.5); (I-a)+(C.2)+(B.6);(I-a)+(C.3)+(B.3); (I-a)+(B.8)+(C.4); (I-a)+(B.2)+(A.4);(I-a)+(C.4)+(A.1); (I-a)+(B.7)+(A.3); (I-a)+(B.7)+(A.4);(I-a)+(C.4)+(A.1); (I-a)+(B.2)+(B.1); (I-a)+(C.4)+(B.2);(I-a)+(B.7)+(B.1); (I-a)+(B.7)+(C.4); (I-a)+(B.6)+(A.4);(I-a)+(B.6)+(A.1); (I-a)+(B.6)+(A.2); (I-a)+(B.5)+(A.1);(I-a)+(B.5)+(A.2); (I-a)+(B.3)+(A.3); (I-a)+(B.3)+(A.4);(I-a)+(B.3)+(A.2); (I-a)+(B.4)+(A.1); (I-a)+(B.4)+(A.2);(I-a)+(C.4)+(B.6); (I-a)+(C.4)+(B.3); (I-a)+(C.1)+(A.4);(I-a)+(C.1)+(A.1); (I-a)+(C.1)+(A.2); (I-a)+(C.1)+(B.1);(I-a)+(C.1)+(B.3); (I-a)+(C.1)+(B.4); (I-a)+(C.3)+(A.3);(I-a)+(C.3)+(A.4); (I-a)+(C.3)+(A.2); (I-a)+(C.3)+(B.1);(I-a)+(C.2)+(A.3); (I-a)+(C.2)+(A.4); (I-a)+(B.8)+(C.1);(I-a)+(B.8)+(C.3); (I-a)+(B.9)+(A.4); (I-a)+(B.9)+(B.1) and(I-a)+(B.9)+(B.6).

Particularly preferred active compound combinations are the followingcombinations selected from the group consisting of: (I-a)+(B.6)+(A.4);(I-a)+(B.6)+(A.1); (I-a)+(B.6)+(A.2); (I-a)+(B.5)+(A.1);(I-a)+(B.5)+(A.2); (I-a)+(B.3)+(A.3); (I-a)+(B.3)+(A.4);(I-a)+(B.3)+(A.2); (I-a)+(B.4)+(A.1); (I-a)+(B.4)+(A.2);(I-a)+(C.4)+(B.6); (I-a)+(C.4)+(B.3); (I-a)+(C.1)+(A.4);(I-a)+(C.1)+(A.1); (I-a)+(C.1)+(A.2); (I-a)+(C.1)+(B.1);(I-a)+(C.1)+(B.3); (I-a)+(C.1)+(B.4); (I-a)+(C.3)+(A.3);(I-a)+(C.3)+(A.4); (I-a)+(C.3)+(A.2); (I-a)+(C.3)+(B.1);(I-a)+(C.2)+(A.3); (I-a)+(C.2)+(A.4); (I-a)+(B.8)+(C.1);(I-a)+(B.8)+(C.3); (I-a)+(B.9)+(A.4); (I-a)+(B.9)+(B.1) and(I-a)+(B.9)+(B.6).

More preferred active compound combinations are the followingcombinations selected from the group consisting of: (I-a)+(B.2)+(A.4);(I-a)+(C.4)+(A.1); (I-a)+(B.7)+(A.3); (I-a)+(B.7)+(A.4);(I-a)+(C.4)+(A.1); (I-a)+(B.2)+(B.1); (I-a)+(C.4)+(B.2);(I-a)+(B.7)+(B.1) and (I-a)+(B.7)+(C.4).

Most preferred active compound combinations are the followingcombinations selected from the group consisting of: (I-a)+(B.1)+(A.3);(I-a)+(B.2)+(A.3); (I-a)+(B.6)+(A.3); (I-a)+(C.4)+(A.3);(I-a)+(C.1)+(A.3); (I-a)+(B.8)+(A.3); (I-a)+(B.1)+(A.4);(I-a)+(C.4)+(A.4); (I-a)+(B.8)+(A.4); (I-a)+(C.4)+(B.1);(I-a)+(C.1)+(B.6); (I-a)+(C.2)+(B.5); (I-a)+(C.2)+(B.6);(I-a)+(C.3)+(B.3) and (I-a)+(B.8)+(C.4).

In the following further active compound combinations comprisingcompounds of the general formula (I-b) and compounds selected from thegroup consisting of (A), (B) and/or (C) are described.

In a first embodiment of the present invention, the compound of thegeneral formula (I-b) is combined with at least one member of (A) thegroup of inhibitors of the ergosterol biosynthesis and at least onemember of (B) the group of inhibitors of the respiratory chain atcomplex I or II.

In a second embodiment of the present invention, the compound of thegeneral formula (I-b) is combined with at least one member of (A) thegroup of inhibitors of the ergosterol biosynthesis and at least onemember of (C) the group of inhibitors of the respiratory chain atcomplex III.

In a third embodiment of the present invention, the compound of thegeneral formula (I-b) is combined with at least one member of (B) thegroup of inhibitors of the respiratory chain at complex I or II and atleast one member of (C) the group of inhibitors of the respiratory chainat complex III.

In a fourth embodiment of the present invention, the compound of thegeneral formula (I-b) is combined with at least two distinct members of(A) the group of inhibitors of the ergosterol biosynthesis.

In a fifth embodiment of the present invention, the compound of thegeneral formula (I-b) is combined with at least two distinct members of(B) the group of inhibitors of the respiratory chain at complex I or II.

In a sixth embodiment of the present invention, the compound of thegeneral formula (I-b) is combined with at least two distinct members of(C) the group of inhibitors of the respiratory chain at complex III.

Preferred active compound combinations are the following combinationsselected from the group consisting of: (I-b)+(B.1)+(A.3);(I-b)+(B.2)+(A.3); (I-b)+(B.6)+(A.3); (I-b)+(C.4)+(A.3);(I-b)+(C.1)+(A.3); (I-b)+(B.8)+(A.3); (I-b)+(B.1)+(A.4);(I-b)+(C.4)+(A.4); (I-b)+(B.8)+(A.4); (I-b)+(C.4)+(B.1);(I-b)+(C.1)+(B.6); (I-b)+(C.2)+(B.5); (I-b)+(C.2)+(B.6);(I-b)+(C.3)+(B.3); (I-b)+(B.8)+(C.4); (I-b)+(B.2)+(A.4);(I-b)+(C.4)+(A.1); (I-b)+(B.7)+(A.3); (I-b)+(B.7)+(A.4);(I-b)+(C.4)+(A.1); (I-b)+(B.2)+(B.1); (I-b)+(C.4)+(B.2);(I-b)+(B.7)+(B.1); (I-b)+(B.7)+(C.4); (I-b)+(B.6)+(A.4);(I-b)+(B.6)+(A.1); (I-b)+(B.6)+(A.2); (I-b)+(B.5)+(A.1);(I-b)+(B.5)+(A.2); (I-b)+(B.3)+(A.3); (I-b)+(B.3)+(A.4);(I-b)+(B.3)+(A.2); (I-b)+(B.4)+(A.1); (I-b)+(B.4)+(A.2);(I-b)+(C.4)+(B.6); (I-b)+(C.4)+(B.3); (I-b)+(C.1)+(A.4);(I-b)+(C.1)+(A.1); (I-b)+(C.1)+(A.2); (I-b)+(C.1)+(B.1);(I-b)+(C.1)+(B.3); (I-b)+(C.1)+(B.4); (I-b)+(C.3)+(A.3);(I-b)+(C.3)+(A.4); (I-b)+(C.3)+(A.2); (I-b)+(C.3)+(B.1);(I-b)+(C.2)+(A.3); (I-b)+(C.2)+(A.4); (I-b)+(B.8)+(C.1);(I-b)+(B.8)+(C.3); (I-b)+(B.9)+(A.4); (I-b)+(B.9)+(B.1) and(I-b)+(B.9)+(B.6).

Particularly preferred active compound combinations are the followingcombinations selected from the group consisting of: (I-b)+(B.6)+(A.4);(I-b)+(B.6)+(A.1); (I-b)+(B.6)+(A.2); (I-b)+(B.5)+(A.1);(I-b)+(B.5)+(A.2); (I-b)+(B.3)+(A.3); (I-b)+(B.3)+(A.4);(I-b)+(B.3)+(A.2); (I-b)+(B.4)+(A.1); (I-b)+(B.4)+(A.2);(I-b)+(C.4)+(B.6); (I-b)+(C.4)+(B.3); (I-b)+(C.1)+(A.4);(I-b)+(C.1)+(A.1); (I-b)+(C.1)+(A.2); (I-b)+(C.1)+(B.1);(I-b)+(C.1)+(B.3); (I-b)+(C.1)+(B.4); (I-b)+(C.3)+(A.3);(I-b)+(C.3)+(A.4); (I-b)+(C.3)+(A.2); (I-b)+(C.3)+(B.1);(I-b)+(C.2)+(A.3); (I-b)+(C.2)+(A.4); (I-b)+(B.8)+(C.1);(I-b)+(B.8)+(C.3); (I-b)+(B.9)+(A.4); (I-b)+(B.9)+(B.1) and(I-b)+(B.9)+(B.6).

More preferred active compound combinations are the followingcombinations selected from the group consisting of: (I-b)+(B.2)+(A.4);(I-b)+(C.4)+(A.1); (I-b)+(B.7)+(A.3); (I-b)+(B.7)+(A.4);(I-b)+(C.4)+(A.1); (I-b)+(B.2)+(B.1); (I-b)+(C.4)+(B.2);(I-b)+(B.7)+(B.1) and (I-b)+(B.7)+(C.4).

Most preferred active compound combinations are the followingcombinations selected from the group consisting of: (I-b)+(B.1)+(A.3);(I-b)+(B.2)+(A.3); (I-b)+(B.6)+(A.3); (I-b)+(C.4)+(A.3);(I-b)+(C.1)+(A.3); (I-b)+(B.8)+(A.3); (I-b)+(B.1)+(A.4);(I-b)+(C.4)+(A.4); (I-b)+(B.8)+(A.4); (I-b)+(C.4)+(B.1);(I-b)+(C.1)+(B.6); (I-b)+(C.2)+(B.5); (I-b)+(C.2)+(B.6);(I-b)+(C.3)+(B.3) and (I-b)+(B.8)+(C.4).

In the following further active compound combinations comprisingcompounds of the general formula (I-c) and compounds selected from thegroup consisting of (A), (B) and/or (C) are described.

In a first embodiment of the present invention, the compound of thegeneral formula (I-c) is combined with at least one member of (A) thegroup of inhibitors of the ergosterol biosynthesis and at least onemember of (B) the group of inhibitors of the respiratory chain atcomplex I or II.

In a second embodiment of the present invention, the compound of thegeneral formula (I-c) is combined with at least one member of (A) thegroup of inhibitors of the ergosterol biosynthesis and at least onemember of (C) the group of inhibitors of the respiratory chain atcomplex III.

In a third embodiment of the present invention, the compound of thegeneral formula (I-c) is combined with at least one member of (B) thegroup of inhibitors of the respiratory chain at complex I or II and atleast one member of (C) the group of inhibitors of the respiratory chainat complex III.

In a fourth embodiment of the present invention, the compound of thegeneral formula (I-c) is combined with at least two members of (A) thegroup of inhibitors of the ergosterol biosynthesis.

In a fifth embodiment of the present invention, the compound of thegeneral formula (I-c) is combined with at least two members of (B) thegroup of inhibitors of the respiratory chain at complex I or II.

In a sixth embodiment of the present invention, the compound of thegeneral formula (I-c) is combined with at least two members of (C) thegroup of inhibitors of the respiratory chain at complex III.

Preferred active compound combinations are the following combinationsselected from the group consisting of: (I-c)+(B.1)+(A.3);(I-c)+(B.2)+(A.3); (I-c)+(B.6)+(A.3); (I-c)+(C.4)+(A.3);(I-c)+(C.1)+(A.3); (I-c)+(B.8)+(A.3); (I-c)+(B.1)+(A.4);(I-c)+(C.4)+(A.4); (I-c)+(B.8)+(A.4); (I-c)+(C.4)+(B.1);(I-c)+(C.1)+(B.6); (I-c)+(C.2)+(B.5); (I-c)+(C.2)+(B.6);(I-c)+(C.3)+(B.3); (I-c)+(B.8)+(C.4); (I-c)+(B.2)+(A.4);(I-c)+(C.4)+(A.1); (I-c)+(B.7)+(A.3); (I-c)+(B.7)+(A.4);(I-c)+(C.4)+(A.1); (I-c)+(B.2)+(B.1); (I-c)+(C.4)+(B.2);(I-c)+(B.7)+(B.1); (I-c)+(B.7)+(C.4); (I-c)+(B.6)+(A.4);(I-c)+(B.6)+(A.1); (I-c)+(B.6)+(A.2); (I-c)+(B.5)+(A.1);(I-c)+(B.5)+(A.2); (I-c)+(B.3)+(A.3); (I-c)+(B.3)+(A.4);(I-c)+(B.3)+(A.2); (I-c)+(B.4)+(A.1); (I-c)+(B.4)+(A.2);(I-c)+(C.4)+(B.6); (I-c)+(C.4)+(B.3); (I-c)+(C.1)+(A.4);(I-c)+(C.1)+(A.1); (I-c)+(C.1)+(A.2); (I-c)+(C.1)+(B.1);(I-c)+(C.1)+(B.3); (I-c)+(C.1)+(B.4); (I-c)+(C.3)+(A.3);(I-c)+(C.3)+(A.4); (I-c)+(C.3)+(A.2); (I-c)+(C.3)+(B.1);(I-c)+(C.2)+(A.3); (I-c)+(C.2)+(A.4); (I-c)+(B.8)+(C.1);(I-c)+(B.8)+(C.3); (I-c)+(B.9)+(A.4); (I-c)+(B.9)+(B.1) and(I-c)+(B.9)+(B.6).

Particularly preferred active compound combinations are the followingcombinations selected from the group consisting of: (I-c)+(B.6)+(A.4);(I-c)+(B.6)+(A.1); (I-c)+(B.6)+(A.2); (I-c)+(B.5)+(A.1);(I-c)+(B.5)+(A.2); (I-c)+(B.3)+(A.3); (I-c)+(B.3)+(A.4);(I-c)+(B.3)+(A.2); (I-c)+(B.4)+(A.1); (I-c)+(B.4)+(A.2);(I-c)+(C.4)+(B.6); (I-c)+(C.4)+(B.3); (I-c)+(C.1)+(A.4);(I-c)+(C.1)+(A.1); (I-c)+(C.1)+(A.2); (I-c)+(C.1)+(B.1);(I-c)+(C.1)+(B.3); (I-c)+(C.1)+(B.4); (I-c)+(C.3)+(A.3);(I-c)+(C.3)+(A.4); (I-c)+(C.3)+(A.2); (I-c)+(C.3)+(B.1);(I-c)+(C.2)+(A.3); (I-c)+(C.2)+(A.4); (I-c)+(B.8)+(C.1);(I-c)+(B.8)+(C.3); (I-c)+(B.9)+(A.4); (I-c)+(B.9)+(B.1) and(I-c)+(B.9)+(B.6).

More preferred active compound combinations are the followingcombinations selected from the group consisting of: (I-c)+(B.2)+(A.4);(I-c)+(C.4)+(A.1); (I-c)+(B.7)+(A.3); (I-c)+(B.7)+(A.4);(I-c)+(C.4)+(A.1); (I-c)+(B.2)+(B.1); (I-c)+(C.4)+(B.2);(I-c)+(B.7)+(B.1) and (I-c)+(B.7)+(C.4).

Most preferred active compound combinations are the followingcombinations selected from the group consisting of: (I-c)+(B.1)+(A.3);(I-c)+(B.2)+(A.3); (I-c)+(B.6)+(A.3); (I-c)+(C.4)+(A.3);(I-c)+(C.1)+(A.3); (I-c)+(B.8)+(A.3); (I-c)+(B.1)+(A.4);(I-c)+(C.4)+(A.4); (I-c)+(B.8)+(A.4); (I-c)+(C.4)+(B.1);(I-c)+(C.1)+(B.6); (I-c)+(C.2)+(B.5); (I-c)+(C.2)+(B.6);(I-c)+(C.3)+(B.3) and (I-c)+(B.8)+(C.4).

In the following further active compound combinations comprisingcompounds of the general formula (I-d) and compounds selected from thegroup consisting of (A), (B) and/or (C) are described.

In a first embodiment of the present invention, the compound of thegeneral formula (I-d) is combined with at least one member of (A) thegroup of inhibitors of the ergosterol biosynthesis and at least onemember of (B) the group of inhibitors of the respiratory chain atcomplex I or II.

In a second embodiment of the present invention, the compound of thegeneral formula (I-d) is combined with at least one member of (A) thegroup of inhibitors of the ergosterol biosynthesis and at least onemember of (C) the group of inhibitors of the respiratory chain atcomplex III.

In a third embodiment of the present invention, the compound of thegeneral formula (I-d) is combined with at least one member of (B) thegroup of inhibitors of the respiratory chain at complex I or II and atleast one member of (C) the group of inhibitors of the respiratory chainat complex III.

In a fourth embodiment of the present invention, the compound of thegeneral formula (I-d) is combined with at least two distinct members of(A) the group of inhibitors of the ergosterol biosynthesis.

In a fifth embodiment of the present invention, the compound of thegeneral formula (I-d) is combined with at least two distinct members of(B) the group of inhibitors of the respiratory chain at complex I or II.

In a sixth embodiment of the present invention, the compound of thegeneral formula (I-d) is combined with at least two distinct members of(C) the group of inhibitors of the respiratory chain at complex III.

Preferred active compound combinations are the following combinationsselected from the group consisting of: (I-d)+(B.1)+(A.3);(I-d)+(B.2)+(A.3); (I-d)+(B.6)+(A.3); (I-d)+(C.4)+(A.3);(I-d)+(C.1)+(A.3); (I-d)+(B.8)+(A.3); (I-d)+(B.1)+(A.4);(I-d)+(C.4)+(A.4); (I-d)+(B.8)+(A.4); (I-d)+(C.4)+(B.1);(I-d)+(C.1)+(B.6); (I-d)+(C.2)+(B.5); (I-d)+(C.2)+(B.6);(I-d)+(C.3)+(B.3); (I-d)+(B.8)+(C.4); (I-d)+(B.2)+(A.4);(I-d)+(C.4)+(A.1); (I-d)+(B.7)+(A.3); (I-d)+(B.7)+(A.4);(I-d)+(C.4)+(A.1); (I-d)+(B.2)+(B.1); (I-d)+(C.4)+(B.2);(I-d)+(B.7)+(B.1); (I-d)+(B.7)+(C.4); (I-d)+(B.6)+(A.4);(I-d)+(B.6)+(A.1); (I-d)+(B.6)+(A.2); (I-d)+(B.5)+(A.1);(I-d)+(B.5)+(A.2); (I-d)+(B.3)+(A.3); (I-d)+(B.3)+(A.4);(I-d)+(B.3)+(A.2); (I-d)+(B.4)+(A.1); (I-d)+(B.4)+(A.2);(I-d)+(C.4)+(B.6); (I-d)+(C.4)+(B.3); (I-d)+(C.1)+(A.4);(I-d)+(C.1)+(A.1); (I-d)+(C.1)+(A.2); (I-d)+(C.1)+(B.1);(I-d)+(C.1)+(B.3); (I-d)+(C.1)+(B.4); (I-d)+(C.3)+(A.3);(I-d)+(C.3)+(A.4); (I-d)+(C.3)+(A.2); (I-d)+(C.3)+(B.1);(I-d)+(C.2)+(A.3); (I-d)+(C.2)+(A.4); (I-d)+(B.8)+(C.1);(I-d)+(B.8)+(C.3); (I-d)+(B.9)+(A.4); (I-d)+(B.9)+(B.1) and(I-d)+(B.9)+(B.6).

Particularly preferred active compound combinations are the followingcombinations selected from the group consisting of: (I-d)+(B.6)+(A.4);(I-d)+(B.6)+(A.1); (I-d)+(B.6)+(A.2); (I-d)+(B.5)+(A.1);(I-d)+(B.5)+(A.2); (I-d)+(B.3)+(A.3); (I-d)+(B.3)+(A.4);(I-d)+(B.3)+(A.2); (I-d)+(B.4)+(A.1); (I-d)+(B.4)+(A.2);(I-d)+(C.4)+(B.6); (I-d)+(C.4)+(B.3); (I-d)+(C.1)+(A.4);(I-d)+(C.1)+(A.1); (I-d)+(C.1)+(A.2); (I-d)+(C.1)+(B.1);(I-d)+(C.1)+(B.3); (I-d)+(C.1)+(B.4); (I-d)+(C.3)+(A.3);(I-d)+(C.3)+(A.4); (I-d)+(C.3)+(A.2); (I-d)+(C.3)+(B.1);(I-d)+(C.2)+(A.3); (I-d)+(C.2)+(A.4); (I-d)+(B.8)+(C.1);(I-d)+(B.8)+(C.3); (I-d)+(B.9)+(A.4); (I-d)+(B.9)+(B.1) and(I-d)+(B.9)+(B.6).

More preferred active compound combinations are the followingcombinations selected from the group consisting of: (I-d)+(B.2)+(A.4);(I-d)+(C.4)+(A.1); (I-d)+(B.7)+(A.3); (I-d)+(B.7)+(A.4);(I-d)+(C.4)+(A.1); (I-d)+(B.2)+(B.1); (I-d)+(C.4)+(B.2);(I-d)+(B.7)+(B.1) and (I-d)+(B.7)+(C.4).

Most preferred active compound combinations are the followingcombinations selected from the group consisting of: (I-d)+(B.1)+(A.3);(I-d)+(B.2)+(A.3); (I-d)+(B.6)+(A.3); (I-d)+(C.4)+(A.3);(I-d)+(C.1)+(A.3); (I-d)+(B.8)+(A.3); (I-d)+(B.1)+(A.4);(I-d)+(C.4)+(A.4); (I-d)+(B.8)+(A.4); (I-d)+(C.4)+(B.1);(I-d)+(C.1)+(B.6); (I-d)+(C.2)+(B.5); (I-d)+(C.2)+(B.6);(I-d)+(C.3)+(B.3) and (I-d)+(B.8)+(C.4).

All named mixing partners of the groups (I), (II) and (III) can, iftheir functional groups enable this, optionally form salts with suitablebases or acids.

Where a compound (I), (II) or (III) can be present in tautomeric form,such a compound is understood hereinabove and herein below also toinclude, where applicable, corresponding tautomeric forms, even whenthese are not specifically mentioned in each case.

The radical definitions and explanations given above in general terms orstated within preferred ranges can, however, also be combined with oneanother as desired, i.e. including between the preferred, particularpreferred, more and most preferred ranges. They apply both to the endproducts and correspondingly to precursors and intermediates. Inaddition, individual definitions may not apply.

In the definitions of the symbols given in the above formulae,collective terms were used which are generally representative of thefollowing substituents:

Halogen: (also in combinations such as haloalkyl, haloalkoxy etc.)fluorine, chlorine, bromine and iodine;

Alkyl: (including in combinations such as alkylthio, alkoxy etc.)saturated, straight-chain or branched hydrocarbyl radicals having 1 to 8carbon atoms, for example C₁-C₆-alkyl, such as methyl, ethyl, propyl,1-methylethyl, butyl, 1-methylpropyl, 2-methylpropyl, 1,1-dimethylethyl,pentyl, 1-methylbutyl, 2-methylbutyl, 3-methylbutyl, 2,2-dimethylpropyl,1-ethylpropyl, hexyl, 1,1-dimethylpropyl, 1,2-dimethylpropyl,1-methylpentyl, 2-methylpentyl, 3-methylpentyl, 4-methylpentyl,1,1-dimethylbutyl, 1,2-dimethylbutyl, 1,3-dimethylbutyl,2,2-dimethylbutyl, 2,3-dimethylbutyl, 3,3-dimethylbutyl, 1-ethylbutyl,2-ethylbutyl, 1,1,2-trimethylpropyl, 1,2,2-trimethylpropyl,1-ethyl-1-methylpropyl and 1-ethyl-2-methylpropyl; heptyl, octyl.

Haloalkyl: (including in combinations such as haloalkylthio, haloalkoxyetc.) straight-chain or branched alkyl groups having 1 to 8 carbon atoms(as specified above), where some or all of the hydrogen atoms in thesegroups may be replaced by halogen atoms as specified above, for exampleC₁-C₃-haloalkyl such as chloromethyl, bromomethyl, dichloromethyl,trichloromethyl, fluoromethyl, difluoromethyl, trifluoromethyl,chlorofluoromethyl, dichlorofluoromethyl, chlorodifluoromethyl,1-chloroethyl, 1-bromoethyl, 1-fluoroethyl, 2-fluoroethyl,2,2-difluoroethyl, 2,2,2-trifluoroethyl, 2-chloro-2-fluoroethyl,2-chloro-2-difluoroethyl, 2,2-dichloro-2-fluoroethyl,2,2,2-trichloroethyl, pentafluoroethyl and 1,1,1-trifluoroprop-2-yl.

Alkenyl: unsaturated, straight-chain or branched hydrocarbyl radicalshaving 2 to 8 carbon atoms and one double bond in any position, forexample C₂-C₆-alkenyl such as ethenyl, 1-propenyl, 2-propenyl,1-methylethenyl, 1-butenyl, 2-butenyl, 3-butenyl, 1-methyl-1-propenyl,2-methyl-1-propenyl, 1-methyl-2-propenyl, 2-methyl-2-propenyl,1-pentenyl, 2-pentenyl, 3-pentenyl, 4-pentenyl, 1-methyl-1-butenyl,2-methyl-1-butenyl, 3-methyl-1-butenyl, 1-methyl-2-butenyl,2-methyl-2-butenyl, 3-methyl-2-butenyl, 1-methyl-3-butenyl,2-methyl-3-butenyl, 3-methyl-3-butenyl, 1,1-dimethyl-2-propenyl,1,2-dimethyl-1-propenyl, 1,2-dimethyl-2-propenyl, 1-ethyl-1-propenyl,1-ethyl-2-propenyl, 1-hexenyl, 2-hexenyl, 3-hexenyl, 4-hexenyl,5-hexenyl, 1-methyl-1-pentenyl, 2-methyl-1-pentenyl,3-methyl-1-pentenyl, 4-methyl-1-pentenyl, 1-methyl-2-pentenyl,2-methyl-2-pentenyl, 3-methyl-2-pentenyl, 4-methyl-2-pentenyl,1-methyl-3-pentenyl, 2-methyl-3-pentenyl, 3-methyl-3-pentenyl,4-methyl-3-pentenyl, 1-methyl-4-pentenyl, 2-methyl-4-pentenyl,3-methyl-4-pentenyl, 4-methyl-4-pentenyl, 1,1-dimethyl-2-butenyl,1,1-dimethyl-3-butenyl, 1,2-dimethyl-1-butenyl, 1,2-dimethyl-2-butenyl,1,2-dimethyl-3-butenyl, 1,3-dimethyl-1-butenyl, 1,3-dimethyl-2-butenyl,1,3-dimethyl-3-butenyl, 2,2-dimethyl-3-butenyl, 2,3-dimethyl-1-butenyl,2,3-dimethyl-2-butenyl, 2,3-dimethyl-3-butenyl, 3,3-dimethyl-1-butenyl,3,3-dimethyl-2-butenyl, 1-ethyl-1-butenyl, 1-ethyl-2-butenyl,1-ethyl-3-butenyl, 2-ethyl-1-butenyl, 2-ethyl-2-butenyl,2-ethyl-3-butenyl, 1,1,2-trimethyl-2-propenyl,1-ethyl-1-methyl-2-propenyl, 1-ethyl-2-methyl-1-propenyl and1-ethyl-2-methyl-2-propenyl.

Cycloalkyl: monocyclic saturated hydrocarbyl groups having 3 to 8 carbonring members, such as cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl,cycloheptyl and cyclooctyl.

Aryl: unsubstituted or substituted, aromatic, mono-, bi- or tricyclicring, for example phenyl, naphthyl, anthracenyl (anthryl),phenanthracenyl (phenanthryl).

Hetaryl: unsubstituted or substituted, unsaturated heterocyclic 5- to7-membered ring containing up to 4 nitrogen atoms or alternatively 1nitrogen atom and up to 2 further heteroatoms selected from N, O and S:for example 2-furyl, 3-furyl, 2-thienyl, 3-thienyl, 2-pyrrolyl,3-pyrrolyl, 1-pyrrolyl, 3-pyrazolyl, 4-pyrazolyl, 5-pyrazolyl,1-pyrazolyl, 1H-imidazol-2-yl, 1H-imidazol-4-yl, 1H-imidazol-5-yl,1H-imidazol-1-yl, 2-oxazolyl, 4-oxazolyl, 5-oxazolyl, 2-thiazolyl,4-thiazolyl, 5-thiazolyl, 3-isoxazolyl, 4-isoxazolyl, 5-isoxazolyl,3-isothiazolyl, 4-isothiazolyl, 5-isothiazolyl, 1H-1,2,3-triazol-1-yl,1H-1,2,3-triazol-4-yl, 1H-1,2,3-triazol-5-yl, 2H-1,2,3-triazol-2-yl,2H-1,2,3-triazol-4-yl, 1H-1,2,4-triazol-3-yl, 1H-1,2,4-triazol-5-yl,1H-1,2,4-triazol-1-yl, 4H-1,2,4-triazol-3-yl, 4H-1,2,4-triazol-4-yl,1H-tetrazol-1-yl, 1H-tetrazol-5-yl, 2H-tetrazol-2-yl, 2H-tetrazol-5-yl,1,2,4-oxadiazol-3-yl, 1,2,4-oxadiazol-5-yl, 1,2,4-thiadiazol-3-yl,1,2,4-thiadiazol-5-yl, 1,3,4-oxadiazol-2-yl, 1,3,4-thiadiazol-2-yl,1,2,3-oxadiazol-4-yl, 1,2,3-oxadiazol-5-yl, 1,2,3-thiadiazol-4-yl,1,2,3-thiadiazol-5-yl, 1,2,5-oxadiazol-3-yl, 1,2,5-thiadiazol-3-yl,2-pyridinyl, 3-pyridinyl, 4-pyridinyl, 3-pyridazinyl, 4-pyridazinyl,2-pyrimidinyl, 4-pyrimidinyl, 5-pyrimidinyl, 2-pyrazinyl,1,3,5-triazin-2-yl, 1,2,4-triazin-3-yl, 1,2,4-triazin-5-yl,1,2,4-triazin-6-yl.

Composition/Formulation

The present invention further relates to a crop protection compositionfor controlling harmful microorganisms, especially phytopathogenicfungi, comprising an effective and non-phytotoxic amount of theinventive active compound combinations. These are preferably fungicidalcrop protection compositions which comprise agriculturally suitableauxiliaries, solvents, carriers, surfactants, extenders or the like.

An “effective and non-phytotoxic amount” means an amount of theinventive active compound combination or composition which is sufficientto control the fungal disease of the plant in a satisfactory manner orto eradicate the fungal disease completely, and which, at the same time,does not cause any significant symptoms of phytotoxicity. In general,this application rate may vary within a relatively wide range. Itdepends on several factors, for example on the fungus to be controlled,the plant, the climatic conditions and the ingredients of the inventiveactive compound combinations or compositions.

The treatment is effected directly or by action on their surroundings,habitat or storage space by the customary treatment methods, for exampleby dipping, spraying, atomizing, irrigating, evaporating, dusting,fogging, broadcasting, foaming, painting, spreading-on, watering(drenching) and drip irrigating. It is also possible to deploy thecompositions by the ultra-low volume method or to inject the compositionpreparation or the compositions itself into the soil.

Suitable organic solvents include all polar and non-polar organicsolvents usually employed for formulation purposes. Preferable thesolvents are selected from ketones, e.g. methyl-isobutyl-ketone andcyclohexanone, amides, e.g. dimethyl formamide and alkanecarboxylic acidamides, e.g. N,N-dimethyl decaneamide and N,N-dimethyl octanamide,furthermore cyclic solvents, e.g. N-methyl-pyrrolidone,N-octyl-pyrrolidone, N-dodecyl-pyrrolidone, N-octyl-caprolactame,N-dodecyl-caprolactame and butyrolactone, furthermore strong polarsolvents, e.g. dimethylsulfoxide, and aromatic hydrocarbons, e.g. xylol,Solvesso™, mineral oils, e.g. white spirit, petroleum, alkyl benzenesand spindle oil, also esters, e.g. propyleneglycol-monomethyletheracetate, adipic acid dibutylester, acetic acid hexylester, acetic acidheptylester, citric acid tri-n-butylester and phthalic aciddi-n-butylester, and also alkohols, e.g. benzyl alcohol and1-methoxy-2-propanol.

According to the invention, a carrier is a natural or synthetic, organicor inorganic substance with which the active compound combinations aremixed or combined for better applicability, in particular forapplication to plants or plant parts or seed. The carrier, which may besolid or liquid, is generally inert and should be suitable for use inagriculture.

Useful solid or liquid carriers include: for example ammonium salts andnatural rock dusts, such as kaolins, clays, talc, chalk, quartz,attapulgite, montmorillonite or diatomaceous earth, and synthetic rockdusts, such as finely divided silica, alumina and natural or syntheticsilicates, resins, waxes, solid fertilizers, water, alcohols, especiallybutanol, organic solvents, mineral and vegetable oils, and derivativesthereof. Mixtures of such carriers can likewise be used.

Suitable solid filler and carrier include inorganic particles, e.g.carbonates, silikates, sulphates and oxides with an average particlesize of between 0.005 and 20 μm, preferably of between 0.02 to 10 μm,for example ammonium sulphate, ammonium phosphate, urea, calciumcarbonate, calcium sulphate, magnesium sulphate, magnesium oxide,aluminium oxide, silicium dioxide, so-called fine-particle silica,silica gels, natural or synthetic silicates, and alumosilicates andplant products like cereal flour, wood powder/sawdust and cellulosepowder.

Useful solid carriers for granules include: for example crushed andfractionated natural rocks such as calcite, marble, pumice, sepiolite,dolomite, and synthetic granules of inorganic and organic meals, andalso granules of organic material such as sawdust, coconut shells, maizecobs and tobacco stalks.

Useful liquefied gaseous extenders or carriers are those liquids whichare gaseous at standard temperature and under standard pressure, forexample aerosol propellants such as halohydrocarbons, and also butane,propane, nitrogen and carbon dioxide.

In the formulations, it is possible to use tackifiers such ascarboxymethylcellulose, and natural and synthetic polymers in the formof powders, granules or latices, such as gum arabic, polyvinyl alcoholand polyvinyl acetate, or else natural phospholipids, such as cephalinsand lecithins, and synthetic phospholipids. Further additives may bemineral and vegetable oils.

If the extender used is water, it is also possible to employ, forexample, organic solvents as auxiliary solvents. Useful liquid solventsare essential: aromatics such as xylene, toluene or alkylnaphthalenes,chlorinated aromatics and chlorinated aliphatic hydrocarbons such aschlorobenzenes, chloroethylenes or dichloromethane, aliphatichydrocarbons such as cyclohexane or paraffins, for example mineral oilfractions, mineral and vegetable oils, alcohols such as butanol orglycol and their ethers and esters, ketones such as acetone, methylethyl ketone, methyl isobutyl ketone or cyclohexanone, strongly polarsolvents such as dimethylformamide and dimethyl sulphoxide, and alsowater.

The inventive compositions may additionally comprise further components,for example surfactants. Useful surfactants are emulsifiers and/or foamformers, dispersants or wetting agents having ionic or nonionicproperties, or mixtures of these surfactants. Examples of these aresalts of polyacrylic acid, salts of lignosulphonic acid, salts ofphenolsulphonic acid or naphthalenesulphonic acid, polycondensates ofethylene oxide with fatty alcohols or with fatty acids or with fattyamines, substituted phenols (preferably alkylphenols or arylphenols),salts of sulphosuccinic esters, taurine derivatives (preferably alkyltaurates), phosphoric esters of polyethoxylated alcohols or phenols,fatty esters of polyols, and derivatives of the compounds containingsulphates, sulphonates and phosphates, for example alkylaryl polyglycolethers, alkylsulphonates, alkylsulphates, arylsulphonates, proteinhydrolysates, lignosulphite waste liquors and methylcellulose. Thepresence of a surfactant is necessary if one of the active ingredientsand/or one of the inert carriers is insoluble in water and whenapplication is effected in water. The proportion of surfactants isbetween 5 and 40 percent by weight of the inventive composition.

Suitable surfactants (adjuvants, emulsifiers, dispersants, protectivecolloids, wetting agent and adhesive) include all common ionic andnon-ionic substances, for example ethoxylated nonylphenols, polyalkyleneglycolether of linear or branched alcohols, reaction products of alkylphenols with ethylene oxide and/or propylene oxide, reaction products offatty acid amines with ethylene oxide and/or propylene oxide,furthermore fattic acid esters, alkyl sulfonates, alkyl sulphates, alkylethersulphates, alkyl etherphosphates, arylsulphate, ethoxylatedarylalkylphenols, e.g. tristyryl-phenol-ethoxylates, furthermoreethoxylated and propoxylated arylalkylphenols like sulphated orphosphated arylalkylphenol-ethoxylates and -ethoxy- and propoxylates.Further examples are natural and synthetic, water soluble polymers, e.g.lignosulphonates, gelatine, gum arabic, phospholipides, starch,hydrophobic modified starch and cellulose derivatives, in particularcellulose ester and cellulose ether, further polyvinyl alcohol,polyvinyl acetate, polyvinyl pyrrolidone, polyacrylic acid,polymethacrylic acid and co-polymerisates of (meth)acrylic acid and(meth)acrylic acid esters, and further co-polymerisates of methacrylicacid and methacrylic acid esters which are neutralized with alkalimetalhydroxide and also condensation products of optionally substitutednaphthalene sulfonic acid salts with formaldehyde.

It is possible to use dyes such as inorganic pigments, for example ironoxide, titanium oxide and Prussian Blue, and organic dyes such asalizarin dyes, azo dyes and metal phthalocyanine dyes, and tracenutrients such as salts of iron, manganese, boron, copper, cobalt,molybdenum and zinc.

Antifoams which may be present in the formulations include e.g. siliconeemulsions, longchain alcohols, fattiy acids and their salts as well asfluoroorganic substances and mixtures thereof.

Examples of thickeners are polysaccharides, e.g. xanthan gum or veegum,silicates, e.g. attapulgite, bentonite as well as fine-particle silica.

If appropriate, it is also possible for other additional components tobe present, for example protective colloids, binders, adhesives,thickeners, thixotropic substances, penetrants, stabilizers,sequestrants, complexing agents. In general, the active ingredients canbe combined with any solid or liquid additive commonly used forformulation purposes.

The inventive active compound combinations or compositions can be usedas such or, depending on their particular physical and/or chemicalproperties, in the form of their formulations or the use forms preparedtherefrom, such as aerosols, capsule suspensions, cold-foggingconcentrates, warm-fogging concentrates, encapsulated granules, finegranules, flowable concentrates for the treatment of seed, ready-to-usesolutions, dustable powders, emulsifiable concentrates, oil-in-wateremulsions, water-in-oil emulsions, macrogranules, microgranules,oil-dispersible powders, oil-miscible flowable concentrates,oil-miscible liquids, gas (under pressure), gas generating product,foams, pastes, pesticide coated seed, suspension concentrates,suspoemulsion concentrates, soluble concentrates, suspensions, wettablepowders, soluble powders, dusts and granules, water-soluble andwater-dispersible granules or tablets, water-soluble andwater-dispersible powders for the treatment of seed, wettable powders,natural products and synthetic substances impregnated with activeingredient, and also microencapsulations in polymeric substances and incoating materials for seed, and also ULV cold-fogging and warm-foggingformulations.

The inventive compositions include not only formulations which arealready ready for use and can be applied with a suitable apparatus tothe plant or the seed, but also commercial concentrates which have to bediluted with water prior to use. Customary applications are for exampledilution in water and subsequent spraying of the resulting spray liquor,application after dilution in oil, direct application without dilution,seed treatment or soil application of granules.

The inventive compositions and formulations generally contain between0.05 and 99% by weight, 0.01 and 98% by weight, preferably between 0.1and 95% by weight, more preferably between 0.5 and 90% of activeingredient, most preferably between 10 and 70% by weight. For specialapplications, e.g. for protection of wood and derived timber productsthe inventive compositions and formulations generally contain between0.0001 and 95% by weight, preferably 0.001 to 60% by weight of activeingredient.

The contents of active ingredient in the application forms prepared fromthe commercial formulations may vary in a broad range. The concentrationof the active ingredients in the application forms is generally between0.000001 to 95% by weight, preferably between 0.0001 and 2% by weight.

The formulations mentioned can be prepared in a manner known per se, forexample by mixing the active ingredients with at least one customaryextender, solvent or diluent, adjuvant, emulsifier, dispersant, and/orbinder or fixative, wetting agent, water repellent, if appropriatedesiccants and UV stabilizers and, if appropriate, dyes and pigments,antifoams, preservatives, inorganic and organic thickeners, adhesives,gibberellins and also further processing auxiliaries and also water.Depending on the formulation type to be prepared further processingsteps are necessary, e.g. wet grinding, dry grinding and granulation.

The inventive active compound combinations may be present as such or intheir (commercial) formulations and in the use forms prepared from theseformulations as a mixture with other (known) active ingredients, such asinsecticides, attractants, sterilants, bactericides, acaricides,nematicides, fungicides, growth regulators, herbicides, fertilizers,safeners and/or semiochemicals.

The inventive treatment of the plants and plant parts with the activecompound combinations or compositions is effected directly or by actionon their surroundings, habitat or storage space by the customarytreatment methods, for example by dipping, spraying, atomizing,irrigating, evaporating, dusting, fogging, broadcasting, foaming,painting, spreading-on, watering (drenching), drip irrigating and, inthe case of propagation material, especially in the case of seeds, alsoby dry seed treatment, wet seed treatment, slurry treatment,incrustation, coating with one or more coats, etc. It is also possibleto deploy the active compound combinations by the ultra-low volumemethod or to inject the active compound combination preparation into thesoil.

Plant/Crop Protection

The inventive active compound combinations or compositions have potentmicrobicidal activity and can be used for control of harmfulmicroorganisms, such as phytopathogenic fungi, in crop protection and inthe protection of materials.

The invention also relates to a method for controlling harmfulmicroorganisms, comprising applying the active compound combination orthe crop protection composition to the plant or the phytopathogenicfungi or the habitat of the plant or the habitat of the phytopathogenicfungi.

Fungicides can be used in crop protection for control of phytopathogenicfungi. They are characterized by an outstanding efficacy against a broadspectrum of phytopathogenic fungi, including soilborne pathogens, whichare in particular members of the classes Plasmodiophoromycetes,Peronosporomycetes (Syn. Oomycetes), Chytridiomycetes, Zygomycetes,Ascomycetes, Basidiomycetes and Deuteromycetes (Syn. Fungi imperfecti).Some fungicides are systemically active and can be used in plantprotection as foliar, seed dressing or soil fungicide. Furthermore, theyare suitable for combating fungi, which inter alia infest wood or rootsof plant.

Bactericides can be used in crop protection for control ofPseudomonadaceae, Rhizobiaceae, Enterobacteriaceae, Corynebacteriaceaeand Streptomycetaceae.

Non-limiting examples of pathogens of fungal diseases which can betreated in accordance with the invention include:

diseases caused by powdery mildew pathogens, for example Blumeriaspecies, for example Blumeria graminis; Podosphaera species, for examplePodosphaera leucotricha; Sphaerotheca species, for example Sphaerothecafuliginea; Uncinula species, for example Uncinula necator;

diseases caused by rust disease pathogens, for example Gymnosporangiumspecies, for example Gymnosporangium sabinae; Hemileia species, forexample Hemileia vastatrix; Phakopsora species, for example Phakopsorapachyrhizi and Phakopsora meibomiae; Puccinia species, for examplePuccinia recondite, P. triticina, P. graminis or P. striiformis;Uromyces species, for example Uromyces appendiculatus;

diseases caused by pathogens from the group of the Oomycetes, forexample Albugo species, for example Algubo candida; Bremia species, forexample Bremia lactucae; Peronospora species, for example Peronosporapisi or P. brassicae; Phytophthora species, for example Phytophthorainfestans; Plasmopara species, for example Plasmopara viticola;Pseudoperonospora species, for example Pseudoperonospora humuli orPseudoperonospora cubensis; Pythium species, for example Pythiumultimum;

leaf blotch diseases and leaf wilt diseases caused, for example, byAlternaria species, for example Alternaria solani; Cercospora species,for example Cercospora beticola; Cladiosporium species, for exampleCladiosporium cucumerinum; Cochliobolus species, for exampleCochliobolus sativus (conidia form: Drechslera, Syn: Helminthosporium),Cochliobolus miyabeanus; Colletotrichum species, for exampleColletotrichum lindemuthanium; Cycloconium species, for exampleCycloconium oleaginum; Diaporthe species, for example Diaporthe citri;Elsinoe species, for example Elsinoe fawcettii; Gloeosporium species,for example Gloeosporium laeticolor; Glomerella species, for exampleGlomerella cingulata; Guignardia species, for example Guignardiabidwelli; Leptosphaeria species, for example Leptosphaeria maculans,Leptosphaeria nodorum; Magnaporthe species, for example Magnaporthegrisea; Microdochium species, for example Microdochium nivale;Mycosphaerella species, for example Mycosphaerella graminicola, M.arachidicola and M. fijiensis; Phaeosphaeria species, for examplePhaeosphaeria nodorum; Pyrenophora species, for example Pyrenophorateres, Pyrenophora tritici repentis; Ramularia species, for exampleRamularia collo-cygni, Ramularia areola; Rhynchosporium species, forexample Rhynchosporium secalis; Septoria species, for example Septoriaapii, Septoria lycopersii; Typhula species, for example Typhulaincarnata; Venturia species, for example Venturia inaequalis;

root and stem diseases caused, for example, by Corticium species, forexample Corticium graminearum; Fusarium species, for example Fusariumoxysporum; Gaeumannomyces species, for example Gaeumannomyces graminis;Rhizoctonia species, such as, for example Rhizoctonia solani;Sarocladium diseases caused for example by Sarocladium oryzae;Sclerotium diseases caused for example by Sclerotium oryzae; Tapesiaspecies, for example Tapesia acuformis; Thielaviopsis species, forexample Thielaviopsis basicola;

ear and panicle diseases (including corn cobs) caused, for example, byAlternaria species, for example Alternaria spp.; Aspergillus species,for example Aspergillus flavus; Cladosporium species, for exampleCladosporium cladosporioides; Claviceps species, for example Clavicepspurpurea; Fusarium species, for example Fusarium culmorum; Gibberellaspecies, for example Gibberella zeae; Monographella species, for exampleMonographella nivalis; Septoria species, for example Septoria nodorum;

diseases caused by smut fungi, for example Sphacelotheca species, forexample Sphacelotheca reiliana; Tilletia species, for example Tilletiacaries, T. controversa; Urocystis species, for example Urocystisocculta; Ustilago species, for example Ustilago nuda, U. nuda tritici;

fruit rot caused, for example, by Aspergillus species, for exampleAspergillus flavus; Botrytis species, for example Botrytis cinerea;Penicillium species, for example Penicillium expansum and P.purpurogenum; Sclerotinia species, for example Sclerotinia sclerotiorum;Verticilium species, for example Verticilium alboatrum;

seed and soilborne decay, mould, wilt, rot and damping-off diseasescaused, for example, by Alternaria species, caused for example byAlternaria brassicicola; Aphanomyces species, caused for example byAphanomyces euteiches; Ascochyta species, caused for example byAscochyta lentis; Aspergillus species, caused for example by Aspergillusflavus; Cladosporium species, caused for example by Cladosporiumherbarum; Cochliobolus species, caused for example by Cochliobolussativus; (Conidiaform: Drechslera, Bipolaris Syn: Helminthosporium);Colletotrichum species, caused for example by Colletotrichum coccodes;Fusarium species, caused for example by Fusarium culmorum; Gibberellaspecies, caused for example by Gibberella zeae; Macrophomina species,caused for example by Macrophomina phaseolina; Monographella species,caused for example by Monographella nivalis; Penicillium species, causedfor example by Penicillium expansum; Phoma species, caused for exampleby Phoma lingam; Phomopsis species, caused for example by Phomopsissojae; Phytophthora species, caused for example by Phytophthoracactorum; Pyrenophora species, caused for example by Pyrenophoragraminea; Pyricularia species, caused for example by Pyricularia oryzae;Pythium species, caused for example by Pythium ultimum; Rhizoctoniaspecies, caused for example by Rhizoctonia solani; Rhizopus species,caused for example by Rhizopus oryzae; Sclerotium species, caused forexample by Sclerotium rolfsii; Septoria species, caused for example bySeptoria nodorum; Typhula species, caused for example by Typhulaincarnata; Verticillium species, caused for example by Verticilliumdahliae;

cancers, galls and witches' broom caused, for example, by Nectriaspecies, for example Nectria galligena;

wilt diseases caused, for example, by Monilinia species, for exampleMonilinia laxa;

leaf blister or leaf curl diseases caused, for example, by Exobasidiumspecies, for example Exobasidium vexans;

Taphrina species, for example Taphrina deformans;

decline diseases of wooden plants caused, for example, by Esca disease,caused for example by Phaemoniella clamydospora, Phaeoacremoniumaleophilum and Fomitiporia mediterranea; Eutypa dyeback, caused forexample by Eutypa lata; Ganoderma diseases caused for example byGanoderma boninense; Rigidoporus diseases caused for example byRigidoporus lignosus;

diseases of flowers and seeds caused, for example, by Botrytis species,for example Botrytis cinerea;

diseases of plant tubers caused, for example, by Rhizoctonia species,for example Rhizoctonia solani; Helminthosporium species, for exampleHelminthosporium solani;

Club root caused, for example, by Plasmodiophora species, for examplePlamodiophora brassicae;

diseases caused by bacterial pathogens, for example Xanthomonas species,for example Xanthomonas campestris pv. oryzae; Pseudomonas species, forexample Pseudomonas syringae pv. lachrymans; Erwinia species, forexample Erwinia amylovora.

In particular, the active compound combinations and compositionsaccording to the invention are suitable for controlling the followingplant diseases: Albugo spp. (white rust) on ornamental plants, vegetablecrops (e.g. A. candida) and sunflowers (e.g. A. tragopogonis);Alternaria spp. (black spot disease, black blotch) on vegetables,oilseed rape (e.g. A. brassicola or A. brassicae), sugar beet (e.g. A.tenuis), fruit, rice, soybeans and also on potatoes (e.g. A. solani orA. alternata) and tomatoes (e.g. A. solani or A. alternata) andAlternaria spp. (black head) on wheat; Aphanomyces spp. on sugar beetand vegetables; Ascochyta spp. on cereals and vegetables, e.g. A.tritici (Ascochyta leaf blight) on wheat and A. hordei on barley;Bipolaris and Drechslera spp. (teleomorph: Cochliobolus spp.), e.g. leafspot diseases (D. maydis and B. zeicola) on corn, e.g. glume blotch (B.sorokiniana) on cereals and e.g. B. oryzae on rice and on lawn; Blumeria(old name: Erysiphe) graminis (powdery mildew) on cereals (e.g. wheat orbarley); Botryosphaeria spp. (‘Slack Dead Arm Disease’) on grapevines(e.g. B. obtusa); Botrytis cinerea (teleomorph: Botryotinia fuckeliana:gray mold, gray rot) on soft fruit and pomaceous fruit (inter aliastrawberries), vegetables (inter alia lettuce, carrots, celeriac andcabbage), oilseed rape, flowers, grapevines, forest crops and wheat (earmold); Bremia lactucae (downy mildew) on lettuce; Ceratocystis (syn.Ophiostoma) spp. (blue stain fungus) on deciduous trees and coniferoustrees, e.g. C. ulmi (Dutch elm disease) on elms; Cercospora spp.(Cereospora leat spot) on corn (e.g. C. zeae-maydis), rice, sugar beet(e.g. C. beticola), sugar cane, vegetables, coffee, soybeans (e.g. C.sojina or C. kikuchil) and rice; Cladosporium spp. on tomato (e.g. C.fulvum: tomato leaf mold) and cereals, e.g. C. herbarum (ear rot) onwheat; Claviceps purpurea (ergot) on cereals; Cochliobolus (anamorph:Helminthosporium or Bipolaris) spp. (leaf spot) on corn (e.g. C.carbonum), cereals (e.g. C. sativus, anamorph: B. sorokiniana: glumeblotch) and rice (for example C. miyabeanus, anamorph: H. oryzae);Colletotrichum (teleomorph: Glomerella) spp. (anthracnosis) on cotton(e.g. C. gossypii), corn (e.g. C. graminicola: stem rot andanthracnosis), soft fruit, potatoes (e.g. C. coccodes: wilt disease),beans (e.g. C. lindemuthianum) and soybeans (e.g. C. truncatum);Corticium spp., e.g. C. sasakii (sheath blight) on rice; Corynesporacassiicola (leaf spot) on soybeans and ornamental plants; Cycloconiumspp., e.g. C. oleaginum on olives; Cylindrocarpon spp. (e.g. fruit treecancer or black foot disease of grapevine, teleomorph: Nectria orNeonectria spp.) on fruit trees, grapevines (e.g. C. liriodendn;teleomorph: Neonectria liriodendri, black foot disease) and manyornamental trees; Dematophora (teleomorph: Rosellinia) necatrix(root/stem rot) on soybeans; Diaporthe spp. e.g. D. phaseolorum (stemdisease) on soybeans; Drechslera (syn. Helminthosporium, teleomorph:Pyrenophora) spp. on corn, cereals, such as barley (e.g. D. teres, netblotch) and on wheat (e.g. D. tritici-repentis: DTR leaf spot), rice andlawn; Esca disease (dieback of grapevine, apoplexia) on grapevines,caused by Formitiporia (syn. Phellinus) punctata, F mediterranea.Phaeomoniella chlamydospora (old name Phaeoacremonium chlamydosporum),Phaeoacremonium aleophilum and/or Botryosphaeria obtusa; Elsinoe spp. onpome fruit (E. pyri) and soft fruit (E. veneta: anthracnosis) and alsograpevines (E. ampelina: anthracnosis); Entyloma oryzae (leaf smut) onrice; Epicoccum spp. (black head) on wheat; Erysiphe spp. (powderymildew) on sugar beet (E. betae), vegetables (e.g. E. pisi), such ascucumber species (e.g. E. cichoracearum) and cabbage species, such asoilseed rape (e.g. E. cruciferarum); Eutypa fata (Eutypa cancer ordieback, anamorph: Cytosporina lata, syn. Libertella blepharis) on fruittrees, grapevines and many ornamental trees; Exserohilum (syn.Helminthosporium) spp. on corn (e.g. E. turcicum); Fusarium (teleomorph:Gibberella) spp. (wilt disease, root and stem rot) on various plants,such as e.g. F. graminearum or F. culmorum (root rot and silver-top) oncereals (e.g. wheat or barley), F. oxysporum on tomatoes, F. solani onsoybeans and F. verticillioides on corn; Gaeumannomyces graminis(takeall) on cereals (e.g. wheat or barley) and corn; Gibberella spp. oncereals (e.g. G. zeae) and rice (e.g. G. fujikuroi: bakanae disease);Glomerella cingulata on grapevines, pomaceous fruit and other plants andG. gossypii on cotton; grainstaining complex on rice; Guignardiabidwellii (black rot) on grapevines; Gymnosporangium spp. on Rosaceaeand juniper, e.g. G. sabinae (pear rust) on pears; Helminthosporium spp.(syn. Drechslera, teleomorph: Cochliobolus) on corn, cereals and rice;Hemileia spp., e.g. H. vastatrix (coffee leaf rust) on coffee;Isariopsis clavispora (syn. Cladosporium vitis) on grapevines;Macrophomina phaseolina (syn. phaseoli) (root/stem rot) on soybeans andcotton; Microdochium (syn. Fusarium) nivale (pink snow mold) on cereals(e.g. wheat or barley); Microsphaera diffusa (powdery mildew) onsoybeans; Monilinia spp., e.g. M. laxa. M. fructicola and M. fructigena(blossom and twig blight) on stone fruit and other Rosaceae;Mycosphaerella spp. on cereals, bananas, soft fruit and peanuts, such ase.g. M. graminicola (anamorph: Septoria tritici, Septoria leaf blotch)on wheat or M. fijiensis (Sigatoka disease) on bananas; Peronospora spp.(downy mildew) on cabbage (e.g. P. brassicae), oilseed rape (e.g. P.parasitica), bulbous plants (e.g. P. destructor), tobacco (P. tabacina)and soybeans (e.g. P. manshurica); Phakopsora pachyrhizi and P.meibomiae (soybean rust) on soybeans; Phialophora spp. e.g. ongrapevines (e.g. P. tracheiphila and P. tetraspora) and soybeans (e.g.P. gregata: stem disease); Phoma lingam (root and stem rot) on oilseedrape and cabbage and P. betae (leaf spot) on sugar beet; Phomopsis spp.on sunflowers, grapevines (e.g. P. viticola: dead-arm disease) andsoybeans (e.g. stem canker/stem blight: P. phaseoli, teleomorph:Diaporthe phaseolorum); Physoderma maydis (brown spot) on corn;Phytophthora spp. (wilt disease, root, leaf, stem and fruit rot) onvarious plants, such as on bell peppers and cucumber species (e.g. P.capsici), soybeans (e.g. P. megasperma, syn. P. sojae), potatoes andtomatoes (e.g. P. infestans. late blight and brown rot) and deciduoustrees (e.g. P. ramorum sudden oak death); Plasmodiophora brassicae(club-root) on cabbage, oilseed rape, radish and other plants;Plasmopara spp., e.g. P. viticola (peronospora of grapevines, downymildew) on grapevines and P. halstedii on sunflowers; Podosphaera spp.(powdery mildew) on Rosaceae, hops, pomaceaus fruit and soft fruit, e.g.P. leucotricha on apple; Polymyxa spp., e.g. on cereals, such as barleyand wheat (P. graminis) and sugar beet (P. betae) and the viral diseasestransmitted thereby; Pseudocercosporella herpotrichoides (eyespot/stembreak, teleomorph: Tapesia yallundae) on cereals. e.g. wheat or barley;Pseudoperonospora (downy mildew) on various plants, e.g. P. cubensis oncucumber species or P. humili on hops; Pseudopezicula tracheiphila(angular leaf scorch, anamorph Phialophora) on grapevines; Puccinia spp.(rust disease) on various plants, e.g. P. triticina (brown rust ofwheat), P. striiformis (yellow rust). P. hordei (dwarf leaf rust), P.graminis (black rust) or P. recondita (brown rust of rye) on cereals,such as e.g. wheat, barley or rye. P. kuehnii on sugar cane and, e.g.,on asparagus (e.g. P. asparagi); Pyrenophora (anamorph: Drechslera)tritici-repentis (speckled leaf blotch) on wheat or P. teres (netblotch) on barley; Pyricularia spp., e.g. P. oryzae (teleomorph:Magnaporthe grisea. rice blast) on rice and P. grisea on lawn andcereals; Pythium spp. (damping-off disease) on lawn, rice, corn, wheat,cotton, oilseed rape, sunflowers, sugar beet, vegetables and otherplants (e.g. P. ultimum or P. aphanidermatum); Ramularia spp., e.g. R.collo-cygni (Ramularia leaf and lawn spot/physiological leaf spot) onbarley and R. bet/cola on sugar beet; Rhizoctonia spp. on cotton, rice,potatoes, lawn, corn, oilseed rape, potatoes, sugar beet, vegetables andon various other plants, for example R. solani (root and stern rot) onsoybeans, R. solani (sheath blight) on rice or R. cerealis (sharpeyespot) on wheat or barley; Rhizopus stolonifer (soft rot) onstrawberries, carrots, cabbage, grapevines and tomato; Rhynchosporiumsecalis (leaf spot) on barley, rye and triticale; Sarocladium oryzae andS. attenuatum (sheath rot) on rice; Sclerotinia spp. (stem or white rot)on vegetable and field crops, such as oilseed rape, sunflowers (e.g.Sclerotinia sclerotiorum) and soybeans (e.g. S. rolfsii), Septoria spp.on various plants, e.g. S. glycines (leaf spot) on soybeans, S. tritici(Septoria leaf blotch) on wheat and S. (syn. Stagonospora) nodorum (leafblotch and glume blotch) on cereals; Uncinula (syn. Erysiphe) necator(powdery mildew, anamorph: Oidium tuckeri) on grapevines; Setospaeriaspp. (leaf spot) on corn (e.g. S. turcicum, syn. Helminthosporiumturcicum) and lawn; Sphacelotheca spp. (head smut) on corn, (e.g. S.reiliana: kernel smut), millet and sugar cane; Sphaerotheca fuliginea(powdery mildew) on cucumber species; Spongospora subterranea (powderyscab) on potatoes and the viral diseases transmitted thereby;Stagonospora spp. on cereals, e.g. S. nodorum (leaf blotch and glumeblotch, teleomorph: Leptosphaeria [syn. Phaeosphaeria] nodorum) onwheat; Synchytrium endobioticum on potatoes (potato wart disease);Taphrina spp., e.g. T. deformans (curly-leaf disease) on peach and T.pruni (plum-pocket disease) on pi ums; Thielaviopsis spp. (black rootrot) on tobacco, pome fruit, vegetable crops, soybeans and cotton, e.g.T. basicola (syn. Chalara elegans); Tilletia spp. (bunt or stinkingsmut) on cereals, such as e.g. T. tritici (syn. T. caries, wheat bunt)and T. controversa (dwarf bunt) on wheat; Typhula incarnata (gray snowmold) on barley or wheat; Urocystis spp., e.g. U. occulta (flag smut) onrye; Uromyces spp. (rust) on vegetable plants, such as beans (e.g. U.appendiculatus, syn. U. phaseolI) and sugar beet (e.g. U. betae);Ustilago spp. (loose smut) on cereals (e.g. U. nuda and U. avaenae),corn (e.g. U. maydis: corn smut) and sugar cane; Venturia spp. (scab) onapples (e.g. V. inaequalis) and pears and Verticillium spp. (leaf andshoot wilt) on various plants, such as fruit trees and ornamental trees,grapevines, soft fruit, vegetable and field crops, such as e.g. V.dahliae on strawberries, oilseed rape, potatoes and tomatoes.

The present invention is also directed to the use of the active compoundcombinations or compositions according to the invention for thetreatment of soybean diseases. The following diseases of soybeans can becontrolled with preference: Fungal diseases on leaves, stems, pods andseeds caused, for example, by Alternaria leaf spot (Alternaria spec.atrans tenuissima), Anthracnose (Colletotrichum gloeosporoides dematiumvar. truncatum), brown spot (Septoria glycines), cercospora leaf spotand blight (Cercospora kikuchii), choanephora leaf blight (Choanephorainfundibulifera trispora (Syn.)), dactuliophora leaf spot (Dactuliophoraglycines), downy mildew (Peronospora manshurica), drechslera blight(Drechslera glycini), frogeye leaf spot (Cercospora sojina),leptosphaerulina leaf spot (Leptosphaerulina trifolii), phyllostica leafspot (Phyllosticta sojaecola), pod and stem blight (Phomopsis sojae),powdery mildew (Microsphaera diffusa), pyrenochaeta leaf spot(Pyrenochaeta glycines), rhizoctonia aerial, foliage, and web blight(Rhizoctonia solani), rust (Phakopsora pachyrhizi, Phakopsorameibomiae), scab (Sphaceloma glycines), stemphylium leaf blight(Stemphylium botryosum), target spot (Corynespora cassiicola). Fungaldiseases on roots and the stem base caused, for example, by black rootrot (Calonectria crotalariae), charcoal rot (Macrophomina phaseolina),fusarium blight or wilt, root rot, and pod and collar rot (Fusariumoxysporum, Fusarium orthoceras, Fusarium semitectum, Fusarium equiseti),mycoleptodiscus root rot (Mycoleptodiscus terrestris), neocosmospora(Neocosmospora vasinfecta), pod and stem blight (Diaporthe phaseolorum),stem canker (Diaporthe phaseolorum var. caulivora), phytophthora rot(Phytophthora megasperma), brown stem rot (Phialophora gregata), pythiumrot (Pythium aphanidermatum, Pythium irregulare, Pythium debaryanum,Pythium myriotylum, Pythium ultimum), rhizoctonia root rot, stem decay,and damping-off (Rhizoctonia solani), sclerotinia stem decay(Sclerotinia sclerotiorum), sclerotinia southern blight (Sclerotiniarolfsii), thielaviopsis root rot (Thielaviopsis basicola).

The present invention is also directed to the use of the active compoundcombinations or compositions according to the invention for thetreatment of cereal diseases. The following diseases of cereals can becontrolled with preference: Ascochyta leaf blight (Ascochyta tritici onwheat and A. hordei on barley), Powdery mildew (e.g. Blumeria graminisf. sp. tritici on wheat and B. graminis f. sp. hordei on barley; Ergot(Claviceps purpurea) (ergot); Net blotch (e.g. Pyrenophora teres onbarley); DTR leaf spot (e.g. D. triticirepentis on wheat); Fusarium headblight (e.g. F. graminearum or F. culmorum); takeall (Gaeumannomycesgraminis); Snow mould (Microdochium (syn. Fusarium) nivale); Septorialeaf blotch (Mycosphaerella graminicola—anamorph: Septoria tritici);Eyespot (Pseudocercosporella herpotrichoides, teleomorph: Tapesiayallundae), brown rust (e.g. P. triticina on wheat), yellow rust (P.striiformis); dwarf leaf rust (P. hordei), black rust (Pucciniagraminis); Ramularia leaf spot (Ramularia collo-cygni); sharpe eye spot(R. cerealis) Rhynchosporium leaf spot (Rhynchosporium secalis);Septoria glume blotch (Septoria nodorum); Smut & bunt diseases (e.g. T.tritici and T. controversa); gray snow mold (Typhula incarnata); loosesmuts (e.g. U. nuda and U. avenae).

Most preference is given to the following soybean diseases: Cercosporakikuchii, Cercospora sojina; Colletotrichum gloeosporoides dematium var.truncatum; Corynespora casiicola; Diaporthe phaseolorum; Microsphaeradiffusa; Peronospora manshurica; Phakopsora species, for examplePhakopsora pachyrhizi and Phakopsora meibomiae (soybean rust);Phytophthora megasperma; Phialophora gregata; Rhizoctonia solani;Sclerotinia sclerotiorum; Septoria spp. e.g. Septoria glycines,Thielaviopsis basicola.

Most preference is given to the following cereal diseases: Blumeriagraminis f. sp. hordei Blumeria graminis f. sp. tritici F. graminearumF. culmorum Gaeumannomyces graminis Microdochium nivale M. graminicola(anamorph: Septoria tritici) Pseudocercosporella herpotrichoides P.triticina P. striiformis P. hordei P. graminis P. recondita Pyrenophoratritici-repentis Pyrenophora teres Ramularia collo-cygni Rhizoctoniacerealis Rhynchosporium secalis Septoria nodorum.

The fact that the active compound combinations or compositions are welltolerated by plants at the concentrations required for controlling plantdiseases allows the treatment of above-ground parts of plants, ofpropagation stock and seeds, and of the soil.

According to the invention all plants and plant parts can be treated. By“plants” is meant all plants and plant populations such as desirable andundesirable wild plants, cultivars and plant varieties (whether or notprotectable by plant variety or plant breeder's rights). Cultivars andplant varieties can be plants obtained by conventional propagation andbreeding methods which can be assisted or supplemented by one or morebiotechnological methods such as by use of double haploids, protoplastfusion, random and directed mutagenesis, molecular or genetic markers orby bioengineering and genetic engineering methods. By “plant parts” ismeant all above ground and below ground parts and organs of plants suchas shoot, leaf, blossom and root, whereby for example leaves, needles,stems, branches, blossoms, fruiting bodies, fruits and seed as well asroots, corms and rhizomes are listed. Crops and vegetative andgenerative propagating material, for example cuttings, corms, rhizomes,runners and seeds also belong to plant parts.

The inventive active compound combinations or compositions, when theyare well tolerated by plants, have favourable homeotherm toxicity andare well tolerated by the environment, are suitable for protectingplants and plant organs, for enhancing harvest yields, for improving thequality of the harvested material. They can preferably be used as cropprotection compositions. They are active against normally sensitive andresistant species and against all or some stages of development.

Plants which can be treated in accordance with the invention include thefollowing main crop plants maize, soya bean, alfalfa, cotton, sunflower,Brassica oil seeds such as Brassica napus (e.g. canola, rapeseed),Brassica rapa, B. juncea (e.g. (field) mustard) and Brassica carinata,Arecaceae sp. (e.g. oilpalm, coconut), rice, wheat, sugar beet, sugarcane, oats, rye, barley, millet and sorghum, triticale, flax, nuts,grapes and vine and various fruit and vegetables from various botanictaxa, e.g. Rosaceae sp. (e.g. pome fruits such as apples and pears, butalso stone fruits such as apricots, cherries, almonds, plums andpeaches, and berry fruits such as strawberries, raspberries, red andblack currant and gooseberry), Ribesioidae sp., Juglandaceae sp.,Betulaceae sp., Anacardiaceae sp., Fagaceae sp., Moraceae sp., Oleaceaesp. (e.g. olive tree), Actinidaceae sp., Lauraceae sp. (e.g. avocado,cinnamon, camphor), Musaceae sp. (e.g. banana trees and plantations),Rubiaceae sp. (e.g. coffee), Theaceae sp. (e.g. tea), Sterculiceae sp.,Rutaceae sp. (e.g. lemons, oranges, mandarins and grapefruit);Solanaceae sp. (e.g. tomatoes, potatoes, peppers, capsicum, aubergines,tobacco), Liliaceae sp., Compositae sp. (e.g. lettuce, artichokes andchicory—including root chicory, endive or common chicory), Umbelliferaesp. (e.g. carrots, parsley, celery and celeriac), Cucurbitaceae sp.(e.g. cucumbers—including gherkins, pumpkins, watermelons, calabashesand melons), Alliaceae sp. (e.g. leeks and onions), Cruciferae sp. (e.g.white cabbage, red cabbage, broccoli, cauliflower, Brussels sprouts, pakchoi, kohlrabi, radishes, horseradish, cress and chinese cabbage),Leguminosae sp. (e.g. peanuts, peas, lentils and beans—e.g. common beansand broad beans), Chenopodiaceae sp. (e.g. Swiss chard, fodder beet,spinach, beetroot), Linaceae sp. (e.g. hemp), Cannabeacea sp. (e.g.cannabis), Malvaceae sp. (e.g. okra, cocoa), Papaveraceae (e.g. poppy),Asparagaceae (e.g. asparagus); useful plants and ornamental plants inthe garden and woods including turf, lawn, grass and Stevia rebaudiana;and in each case genetically modified types of these plants.

Plant Growth Regulation

In some cases, the active compound combinations or compositions can, atparticular concentrations or application rates, also be used asherbicides, safeners, growth regulators or agents to improve plantproperties, or as microbicides, for example as fungicides, antimycotics,bactericides, viricides (including compositions against viroids) or ascompositions against MLO (Mycoplasma-like organisms) and RLO(Rickettsia-like organisms). If appropriate, they can also be used asintermediates or precursors for the synthesis of other activeingredients.

The inventive active compound combinations intervene in the metabolismof the plants and can therefore also be used as growth regulators.

Plant growth regulators may exert various effects on plants. The effectof the substances depends essentially on the time of application inrelation to the developmental stage of the plant, and also on theamounts of active compound combination or composition applied to theplants or their environment and on the type of application. In eachcase, growth regulators should have a particular desired effect on thecrop plants.

Plant growth-regulating compounds can be used, for example, to inhibitthe vegetative growth of the plants. Such inhibition of growth is ofeconomic interest, for example, in the case of grasses, since it is thuspossible to reduce the frequency of grass cutting in ornamental gardens,parks and sport facilities, on roadsides, at airports or in fruit crops.Also of significance is the inhibition of the growth of herbaceous andwoody plants on roadsides and in the vicinity of pipelines or overheadcables, or quite generally in areas where vigorous plant growth isunwanted.

Also important is the use of growth regulators for inhibition of thelongitudinal growth of cereal. This reduces or completely eliminates therisk of lodging of the plants prior to harvest. In addition, growthregulators in the case of cereals can strengthen the culm, which alsocounteracts lodging. The employment of growth regulators for shorteningand strengthening culms allows the deployment of higher fertilizervolumes to increase the yield, without any risk of lodging of the cerealcrop.

In many crop plants, inhibition of vegetative growth allows denserplanting, and it is thus possible to achieve higher yields based on thesoil surface. Another advantage of the smaller plants obtained in thisway is that the crop is easier to cultivate and harvest.

Inhibition of the vegetative plant growth may also lead to enhancedyields because the nutrients and assimilates are of more benefit toflower and fruit formation than to the vegetative parts of the plants.

Frequently, growth regulators can also be used to promote vegetativegrowth. This is of great benefit when harvesting the vegetative plantparts. However, promoting vegetative growth may also promote generativegrowth in that more assimilates are formed, resulting in more or largerfruits.

In some cases, yield increases may be achieved by manipulating themetabolism of the plant, without any detectable changes in vegetativegrowth. In addition, growth regulators can be used to alter thecomposite of the plants, which in turn may result in an improvement inquality of the harvested products. For example, it is possible toincrease the sugar content in sugar beet, sugar cane, pineapples and incitrus fruit, or to increase the protein content in soya or cereals. Itis also possible, for example, to use growth regulators to inhibit thedegradation of desirable ingredients, for example sugar in sugar beet orsugar cane, before or after harvest. It is also possible to positivelyinfluence the production or the elimination of secondary plantingredients. One example is the stimulation of the flow of latex inrubber trees.

Under the influence of growth regulators, parthenocarpic fruits may beformed. In addition, it is possible to influence the sex of the flowers.It is also possible to produce sterile pollen, which is of greatimportance in the breeding and production of hybrid seed.

Use of growth regulators can control the branching of the plants. On theone hand, by breaking apical dominance, it is possible to promote thedevelopment of side shoots, which may be highly desirable particularlyin the cultivation of ornamental plants, also in combination with aninhibition of growth. On the other hand, however, it is also possible toinhibit the growth of the side shoots. This effect is of particularinterest, for example, in the cultivation of tobacco or in thecultivation of tomatoes.

Under the influence of growth regulators, the amount of leaves on theplants can be controlled such that defoliation of the plants is achievedat a desired time. Such defoliation plays a major role in the mechanicalharvesting of cotton, but is also of interest for facilitatingharvesting in other crops, for example in viticulture. Defoliation ofthe plants can also be undertaken to lower the transpiration of theplants before they are transplanted.

Growth regulators can likewise be used to regulate fruit dehiscence. Onthe one hand, it is possible to prevent premature fruit dehiscence. Onthe other hand, it is also possible to promote fruit dehiscence or evenflower abortion to achieve a desired mass (“thinning”), in order toeliminate alternation. Alternation is understood to mean thecharacteristic of some fruit species, for endogenous reasons, to deliververy different yields from year to year. Finally, it is possible to usegrowth regulators at the time of harvest to reduce the forces requiredto detach the fruits, in order to allow mechanical harvesting or tofacilitate manual harvesting.

Growth regulators can also be used to achieve faster or else delayedripening of the harvested material before or after harvest. This isparticularly advantageous as it allows optimal adjustment to therequirements of the market. Moreover, growth regulators in some casescan improve the fruit colour. In addition, growth regulators can also beused to concentrate maturation within a certain period of time. Thisestablishes the prerequisites for complete mechanical or manualharvesting in a single operation, for example in the case of tobacco,tomatoes or coffee.

By using growth regulators, it is additionally possible to influence theresting of seed or buds of the plants, such that plants such aspineapple or ornamental plants in nurseries, for example, germinate,sprout or flower at a time when they are normally not inclined to do so.In areas where there is a risk of frost, it may be desirable to delaybudding or germination of seeds with the aid of growth regulators, inorder to avoid damage resulting from late frosts.

Finally, growth regulators can induce resistance of the plants to frost,drought or high salinity of the soil. This allows the cultivation ofplants in regions which are normally unsuitable for this purpose.

Resistance Induction/Plant Health and Other Effects

The active compound combinations or compositions according to theinvention also exhibit a potent strengthening effect in plants.Accordingly, they can be used for mobilizing the defences of the plantagainst attack by undesirable microorganisms.

Plant-strengthening (resistance-inducing) substances are to beunderstood as meaning, in the present context, those substances whichare capable of stimulating the defence system of plants in such a waythat the treated plants, when subsequently inoculated with undesirablemicroorganisms, develop a high degree of resistance to thesemicroorganisms.

The active compound combinations or compositions according to theinvention are also suitable for increasing the yield of crops. Inaddition, they show reduced toxicity and are well tolerated by plants.

Further, in context with the present invention plant physiology effectscomprise the following:

Abiotic stress tolerance, comprising temperature tolerance, droughttolerance and recovery after drought stress, water use efficiency(correlating to reduced water consumption), flood tolerance, ozonestress and UV tolerance, tolerance towards chemicals like heavy metals,salts, pesticides (safener) etc.

Biotic stress tolerance, comprising increased fungal resistance andincreased resistance against nematodes, viruses and bacteria. In contextwith the present invention, biotic stress tolerance preferably comprisesincreased fungal resistance.

Increased plant vigor, comprising plant health/plant quality and seedvigor, reduced stand failure, improved appearance, increased recovery,improved greening effect and improved photosynthetic efficiency.

Effects on plant hormones and/or functional enzymes.

Effects on growth regulators (promoters), comprising earliergermination, better emergence, more developed root system and/orimproved root growth, increased ability of tillering, more productivetillers, earlier flowering, increased plant height and/or biomass,shorting of stems, improvements in shoot growth, number of kernels/ear,number of ears/m², number of stolons and/or number of flowers, enhancedharvest index, bigger leaves, less dead basal leaves, improvedphyllotaxy, earlier maturation/earlier fruit finish, homogenous riping,increased duration of grain filling, better fruit finish, biggerfruit/vegetable size, sprouting resistance and reduced lodging.

Increased yield, referring to total biomass per hectare, yield perhectare, kernel/fruit weight, seed size and/or hectoliter weight as wellas to increased product quality, comprising:

Improved processability relating to size distribution (kernel, fruit,etc.), homogenous riping, grain moisture, better milling, bettervinification, better brewing, increased juice yield, harvestability,digestibility, sedimentation value, falling number, pod stability,storage stability, improved fiber length/strength/uniformity, increaseof milk and/or meet quality of silage fed animals, adaption to cookingand frying;

Further comprising improved marketability relating to improvedfruit/grain quality, size distribution (kernel, fruit, etc.), increasedstorage/shelf-life, firmness/softness, taste (aroma, texture, etc.),grade (size, shape, number of berries, etc.), number of berries/fruitsper bunch, crispness, freshness, coverage with wax, frequency ofphysiological disorders, colour, etc.;

Further comprising increased desired ingredients such as e.g. proteincontent, fatty acids, oil content, oil quality, aminoacid composition,sugar content, acid content (pH), sugar/acid ratio (Brix), polyphenols,starch content, nutritional quality, gluten content/index, energycontent, taste, etc.;

And further comprising decreased undesired ingredients such as e.g. lessmycotoxines, less aflatoxines, geosmin level, phenolic aromas, lacchase,polyphenol oxidases and peroxidases, nitrate content etc.

Sustainable agriculture, comprising nutrient use efficiency, especiallynitrogen (N)-use efficiency, phosphours (P)-use efficiency, water useefficiency, improved transpiration, respiration and/or CO₂ assimilationrate, better nodulation, improved Ca-metabolism etc.

Delayed senescence, comprising improvement of plant physiology which ismanifested, for example, in a longer grain filling phase, leading tohigher yield, a longer duration of green leaf colouration of the plantand thus comprising colour (greening), water content, dryness etc.Accordingly, in the context of the present invention, it has been foundthat the specific inventive application of the active compoundcombination makes it possible to prolong the green leaf area duration,which delays the maturation (senescence) of the plant. The mainadvantage to the farmer is a longer grain filling phase leading tohigher yield. There is also an advantage to the farmer on the basis ofgreater flexibility in the harvesting time.

Therein “sedimentation value” is a measure for protein quality anddescribes according to Zeleny (Zeleny value) the degree of sedimentationof flour suspended in a lactic acid solution during a standard timeinterval. This is taken as a measure of the baking quality. Swelling ofthe gluten fraction of flour in lactic acid solution affects the rate ofsedimentation of a flour suspension. Both a higher gluten content and abetter gluten quality give rise to slower sedimentation and higherZeleny test values. The sedimentation value of flour depends on thewheat protein composite and is mostly correlated to the protein content,the wheat hardness, and the volume of pan and hearth loaves. A strongercorrelation between loaf volume and Zeleny sedimentation volume comparedto SDS sedimentation volume could be due to the protein contentinfluencing both the volume and Zeleny value (Czech J. Food Sci. Vol.21, No. 3: 91-96, 2000).

Further the “falling number” as mentioned herein is a measure for thebaking quality of cereals, especially of wheat. The falling number testindicates that sprout damage may have occurred. It means that changes tothe physical properties of the starch portion of the wheat kernel hasalready happened. Therein, the falling number instrument analyzesviscosity by measuring the resistance of a flour and water paste to afalling plunger. The time (in seconds) for this to happen is known asthe falling number. The falling number results are recorded as an indexof enzyme activity in a wheat or flour sample and results are expressedin time as seconds. A high falling number (for example, above 300seconds) indicates minimal enzyme activity and sound quality wheat orflour. A low falling number (for example, below 250 seconds) indicatessubstantial enzyme activity and sprout-damaged wheat or flour.

The term “more developed root system”/“improved root growth” refers tolonger root system, deeper root growth, faster root growth, higher rootdry/fresh weight, higher root volume, larger root surface area, biggerroot diameter, higher root stability, more root branching, higher numberof root hairs, and/or more root tips and can be measured by analyzingthe root architecture with suitable methodologies and Image analysisprogrammes (e.g. WinRhizo).

The term “crop water use efficiency” refers technically to the mass ofagriculture produce per unit water consumed and economically to thevalue of product(s) produced per unit water volume consumed and can e.g.be measured in terms of yield per ha, biomass of the plants,thousand-kernel mass, and the number of ears per m2.

The term “nitrogen-use efficiency” refers technically to the mass ofagriculture produce per unit nitrogen consumed and economically to thevalue of product(s) produced per unit nitrogen consumed, reflectinguptake and utilization efficiency.

Improvement in greening/improved colour and improved photosyntheticefficiency as well as the delay of senescence can be measured withwell-known techniques such as a HandyPea system (Hansatech). Fv/Fm is aparameter widely used to indicate the maximum quantum efficiency ofphotosystem II (PSII). This parameter is widely considered to be aselective indication of plant photosynthetic performance with healthysamples typically achieving a maximum Fv/Fm value of approx. 0.85.Values lower than this will be observed if a sample has been exposed tosome type of biotic or abiotic stress factor which has reduced thecapacity for photochemical quenching of energy within PSII. Fv/Fm ispresented as a ratio of variable fluorescence (Fv) over the maximumfluorescence value (Fm). The Performance Index is essentially anindicator of sample vitality. (See e.g. Advanced Techniques in SoilMicrobiology, 2007, 11, 319-341; Applied Soil Ecology, 2000, 15,169-182.)

The improvement in greening/improved colour and improved photosyntheticefficiency as well as the delay of senescence can also be assessed bymeasurement of the net photosynthetic rate (Pn), measurement of thechlorophyll content, e.g. by the pigment extraction method of Zieglerand Ehle, measurement of the photochemical efficiency (Fv/Fm ratio),determination of shoot growth and final root and/or canopy biomass,determination of tiller density as well as of root mortality.

Within the context of the present invention preference is given toimproving plant physiology effects which are selected from the groupcomprising: enhanced root growth/more developed root system, improvedgreening, improved water use efficiency (correlating to reduced waterconsumption), improved nutrient use efficiency, comprising especiallyimproved nitrogen (N)-use efficiency, delayed senescence and enhancedyield.

Within the enhancement of yield preference is given as to an improvementin the sedimentation value and the falling number as well as to theimprovement of the protein and sugar content—especially with plantsselected from the group of cereals (preferably wheat).

Preferably the novel use of the fungicidal active compound combinationsor compositions of the present invention relates to a combined use of a)reducing damage of plants and plant parts or losses in harvested fruitsor vegetables caused by phytopathogenic fungi by controlling suchphytopathogenic fungi, with or without resistance management, and b) atleast one of enhanced root growth, improved greening, improved water useefficiency, delayed senescence and enhanced yield.

Seed Treatment

The invention further comprises a method for treating seed.

The invention further relates to seed which has been treated by one ofthe methods described in the previous paragraph. The inventive seeds areemployed in methods for the protection of seed from harmfulmicroorganisms such as e.g. phytopathogenic fungi. In these methods,seed treated with at least one inventive active compound combination isused.

The inventive active compound combinations or compositions are alsosuitable for treating seed. A large part of the damage to crop plantscaused by harmful organisms is triggered by the infection of the seedduring storage or after sowing, and also during and after germination ofthe plant. This phase is particularly critical since the roots andshoots of the growing plant are particularly sensitive, and even minordamage may result in the death of the plant. There is therefore a greatinterest in protecting the seed and the germinating plant by usingappropriate compositions.

The control of phytopathogenic fungi by treating the seed of plants hasbeen known for a long time and is the subject of constant improvements.However, the treatment of seed entails a series of problems which cannotalways be solved in a satisfactory manner. For instance, it is desirableto develop methods for protecting the seed and the germinating plant,which dispense with, or at least significantly reduce, the additionaldeployment of crop protection compositions after planting or afteremergence of the plants. It is also desirable to optimize the amount ofthe active compound combination used so as to provide the best possibleprotection for the seed and the germinating plant from attack byphytopathogenic fungi, but without damaging the plant itself by theactive compound combination employed. In particular, methods for thetreatment of seed should also take account of the intrinsic fungicidalproperties of transgenic plants in order to achieve optimal protectionof the seed and the germinating plant with a minimum expenditure of cropprotection compositions.

The present invention therefore also relates to a method for protectionof seed and germinating plants from attack by phytopathogenic fungi, bytreating the seed with an inventive composition. The invention likewiserelates to the use of the inventive compositions for treatment of seedto protect the seed and the germinating plant from phytopathogenicfungi. The invention further relates to seed which has been treated withan inventive composition for protection from phytopathogenic fungi.

The control of phytopathogenic fungi which damage plants post-emergenceis effected primarily by treating the soil and the above-ground parts ofplants with crop protection compositions. Owing to the concernsregarding a possible influence of the crop protection compositions onthe environment and the health of humans and animals, there are effortsto reduce the amount of active ingredients deployed.

One of the advantages of the present invention is that the particularsystemic properties of the inventive active compound combinations andcompositions mean that treatment of the seed with these active compoundcombinations and compositions not only protects the seed itself, butalso the resulting plants after emergence, from phytopathogenic fungi.In this way, the immediate treatment of the crop at the time of sowingor shortly thereafter can be dispensed with.

It is likewise considered to be advantageous that the inventive activecompound combinations or compositions can especially also be used withtransgenic seed, in which case the plant growing from this seed iscapable of expressing a protein which acts against plant pests and/orphytopathogenic fungi. By virtue of the treatment of such seed with theinventive active compound combinations or compositions, merely theexpression of the protein, for example an insecticidal protein, cancontrol certain plant pests and/or phytopathogenic fungi. Surprisingly,a further synergistic effect can be observed in this case, whichadditionally increases the effectiveness for protection against attackby plant pests and/or phytopathogenic fungi.

The inventive compositions are suitable for protecting seed of any plantvariety which is used in agriculture, in greenhouses, in forests or inhorticulture and viticulture. In particular, this is the seed of cereals(such as wheat, barley, rye, triticale, sorghum/millet and oats), maize,cotton, soya beans, rice, potatoes, sunflower, bean, coffee, beet (forexample sugar beet and fodder beet), peanut, oilseed rape, poppy, olive,coconut, cocoa, sugar cane, tobacco, vegetables (such as tomato,cucumbers, onions and lettuce), turf and ornamentals (see also below).The treatment of the seed of cereals (such as wheat, barley, rye,triticale and oats), maize and rice is of particular significance.

As also described below, the treatment of transgenic seed with theinventive active compound combinations or compositions is of particularsignificance. This relates to the seed of plants containing at least oneheterologous gene which enables the expression of a polypeptide orprotein having insecticidal properties. The heterologous gene intransgenic seed can originate, for example, from microorganisms of thespecies Bacillus, Rhizobium, Pseudomonas, Serratia, Trichoderma,Clavibacter, Glomus or Gliocladium. This heterologous gene preferablyoriginates from Bacillus sp., in which case the gene product iseffective against the European maize borer and/or the Western maizerootworm. The heterologous gene more preferably originates from Bacillusthuringiensis.

In the context of the present invention, the active compound combinationis applied to the seed alone or in a suitable formulation (i.e. as acomposition). Preferably, the seed is treated in a state in which it issufficiently stable for no damage to occur in the course of treatment.In general, the seed can be treated at any time between harvest andsowing. It is customary to use seed which has been separated from theplant and freed from cobs, shells, stalks, coats, hairs or the flesh ofthe fruits. For example, it is possible to use seed which has beenharvested, cleaned and dried down to a moisture content of less than 15%by weight. Alternatively, it is also possible to use seed which, afterdrying, for example, has been treated with water and then dried again.

When treating the seed, care must generally be taken that the amount ofthe active compound combination or composition applied to the seedand/or the amount of further additives is selected such that thegermination of the seed is not impaired, or that the resulting plant isnot damaged. This has to be borne in mind in particular in the case ofactive ingredients which can have phytotoxic effects at certainapplication rates.

The inventive active compound combinations can be applied directly, i.e.without containing any other components and without having been diluted.In general, it is preferable to apply the active compound combinationsto the seed in the form of a suitable formulation. Suitable formulationsand methods for seed treatment are known to those skilled in the art andare described, for example, in the following documents: U.S. Pat. No.4,272,417, U.S. Pat. No. 4,245,432, U.S. Pat. No. 4,808,430, U.S. Pat.No. 5,876,739, US 2003/0176428 A1, WO 2002/080675, WO 2002/028186.

The active compound combinations usable in accordance with the inventioncan be converted to the customary seed dressing formulations, such assolutions, emulsions, suspensions, powders, foams, slurries or othercoating compositions for seed, and also ULV formulations.

These formulations are prepared in a known manner, by mixing the activecompound combinations with customary additives, for example customaryextenders and also solvents or diluents, dyes, wetting agents,dispersants, emulsifiers, antifoams, preservatives, secondarythickeners, adhesives, gibberellins and also water.

Useful dyes which may be present in the seed dressing formulationsusable in accordance with the invention are all dyes which are customaryfor such purposes. It is possible to use either pigments, which aresparingly soluble in water, or dyes, which are soluble in water.Examples include the dyes known by the names Rhodamine B, C.I. PigmentRed 112 and C.I. Solvent Red 1.

Useful wetting agents which may be present in the seed dressingformulations usable in accordance with the invention are all substanceswhich promote wetting and which are conventionally used for theformulation of active agrochemical ingredients. Preference is given tousing alkyl naphthalenesulphonates, such as diisopropyl or diisobutylnaphthalenesulphonates.

Useful dispersants and/or emulsifiers which may be present in the seeddressing formulations usable in accordance with the invention are allnonionic, anionic and cationic dispersants conventionally used for theformulation of active agrochemical ingredients. Usable with preferenceare nonionic or anionic dispersants or mixtures of nonionic or anionicdispersants. Suitable nonionic dispersants include especially ethyleneoxide/propylene oxide block polymers, alkylphenol polyglycol ethers andtristryrylphenol polyglycol ether, and the phosphated or sulphatedderivatives thereof. Suitable anionic dispersants are especiallylignosulphonates, polyacrylic acid salts and arylsulphonate/formaldehydecondensates.

Antifoams which may be present in the seed dressing formulations usablein accordance with the invention are all foam-inhibiting substancesconventionally used for the formulation of active agrochemicalingredients. Silicone antifoams and magnesium stearate can be used withpreference.

Preservatives which may be present in the seed dressing formulationsusable in accordance with the invention are all substances usable forsuch purposes in crop protection compositions. Examples includedichlorophene and benzyl alcohol hemiformal.

Secondary thickeners which may be present in the seed dressingformulations usable in accordance with the invention are all substancesusable for such purposes in crop protection compositions. Preferredexamples include cellulose derivatives, acrylic acid derivatives,xanthan, modified clays and finely divided silica.

Adhesives which may be present in the seed dressing formulations usablein accordance with the invention are all customary binders usable inseed dressing products. Preferred examples include polyvinylpyrrolidone,polyvinyl acetate, polyvinyl alcohol and tylose.

The gibberellins which may be present in the seed dressing formulationsusable in accordance with the invention may preferably be gibberellinsA1, A3 (=gibberellic acid), A4 and A7; particular preference is given tousing gibberellic acid. The gibberellins are known (cf. R. Wegler“Chemie der Pflanzenschutz- and Schädlingsbekämpfungsmittel” [Chemistryof the Crop Protection Compositions and Pesticides], vol. 2, SpringerVerlag, 1970, p. 401-412).

The seed dressing formulations usable in accordance with the inventioncan be used, either directly or after previously having been dilutedwith water, for the treatment of a wide range of different seed,including the seed of transgenic plants. In this case, additionalsynergistic effects may also occur in interaction with the substancesformed by expression.

For treatment of seed with the seed dressing formulations usable inaccordance with the invention, or the preparations prepared therefrom byadding water, all mixing units usable customarily for the seed dressingare useful. Specifically, the procedure in the seed dressing is to placethe seed into a mixer, to add the particular desired amount of seeddressing formulations, either as such or after prior dilution withwater, and to mix everything until the formulation is distributedhomogeneously on the seed. If appropriate, this is followed by a dryingprocess.

Mycotoxins

In addition, the inventive active compound combinations or compositionscan reduce the mycotoxin content in the harvested material and the foodsand feeds prepared therefrom. Mycotoxins include particularly, but notexclusively, the following: deoxynivalenol (DON), nivalenol, 15-Ac-DON,3-Ac-DON, T2- and HT2-toxin, fumonisins, zearalenon, moniliformin,fusarin, diaceotoxyscirpenol (DAS), beauvericin, enniatin,fusaroproliferin, fusarenol, ochratoxins, patulin, ergot alkaloids andaflatoxins which can be produced, for example, by the following fungi:Fusarium spec., such as F. acuminatum, F. asiaticum, F. avenaceum, F.crookwellense, F. culmorum, F. graminearum (Gibberella zeae), F.equiseti, F. fujikoroi, F. musarum, F. oxysporum, F. proliferatum, F.poae, F. pseudograminearum, F. sambucinum, F. scirpi, F. semitectum, F.solani, F. sporotrichoides, F. langsethiae, F. subglutinans, F.tricinctum, F. verticillioides etc., and also by Aspergillus spec., suchas A. flavus, A. parasiticus, A. nomius, A. ochraceus, A. clavatus, A.terreus, A. versicolor, Penicillium spec., such as P. verrucosum, P.viridicatum, P. citrinum, P. expansum, P. claviforme, P. roqueforti,Claviceps spec., such as C. purpurea, C. fusiformis, C. paspali, C.africana, Stachybotrys spec. and others.

Material Protection

The inventive active compound combinations or compositions can also beused in the protection of materials, for protection of industrialmaterials against attack and destruction by harmful microorganisms, forexample fungi and insects.

In addition, the active compound combinations or compositions can beused as antifouling compositions, alone or in combinations with otheractive ingredients.

Industrial materials in the present context are understood to meaninanimate materials which have been prepared for use in industry. Forexample, industrial materials which are to be protected by inventiveactive compound combinations from microbial alteration or destructionmay be adhesives, glues, paper, wallpaper and board/cardboard, textiles,carpets, leather, wood, fibers and tissues, paints and plastic articles,cooling lubricants and other materials which can be infected with ordestroyed by microorganisms. Parts of production plants and buildings,for example cooling-water circuits, cooling and heating systems andventilation and air-conditioning units, which may be impaired by theproliferation of microorganisms may also be mentioned within the scopeof the materials to be protected. Industrial materials within the scopeof the present invention preferably include adhesives, sizes, paper andcard, leather, wood, paints, cooling lubricants and heat transferfluids, more preferably wood.

The inventive active compound combinations or compositions may preventadverse effects, such as rotting, decay, discoloration, decoloration orformation of mould.

In the case of treatment of wood the active compound combinations orcompositions according to the invention may also be used against fungaldiseases liable to grow on or inside timber. The term “timber” means alltypes of species of wood, and all types of working of this wood intendedfor construction, for example solid wood, highdensity wood, laminatedwood, and plywood. The method for treating timber according to theinvention mainly consists in contacting one or more active compoundcombinations or compositions according to the invention; this includesfor example direct application, spraying, dipping, injection or anyother suitable means.

In addition, the active compound combinations or compositions can beused to protect objects which come into contact with saltwater orbrackish water, especially hulls, screens, nets, buildings, moorings andsignalling systems, from fouling.

The inventive method for controlling phytopathogenic fungi can also beemployed for protecting storage goods. Storage goods are understood tomean natural substances of vegetable or animal origin or processedproducts thereof which are of natural origin, and for which long-termprotection is desired. Storage goods of vegetable origin, for exampleplants or plant parts, such as stems, leaves, tubers, seeds, fruits,grains, can be protected freshly harvested or after processing by(pre)drying, moistening, comminuting, grinding, pressing or roasting.Storage goods also include timber, both unprocessed, such asconstruction timber, electricity poles and barriers, or in the form offinished products, such as furniture. Storage goods of animal originare, for example, hides, leather, furs and hairs. The inventive activecompound combinations or compositions may prevent adverse effects, suchas rotting, decay, discoloration, decoloration or formation of mould.

Microorganisms capable of degrading or altering the industrial materialsinclude, for example, bacteria, fungi, yeasts, algae and slimeorganisms. The inventive active compound combinations preferably actagainst fungi, especially moulds, wood-discoloring and wood-destroyingfungi (Ascomycetes, Basidiomycetes, Deuteromycetes and Zygomycetes), andagainst slime organisms and algae. Examples include microorganisms ofthe following genera: Alternaria, such as Alternaria tenuis;Aspergillus, such as Aspergillus niger; Chaetomium, such as Chaetomiumglobosum; Coniophora, such as Coniophora puetana; Lentinus, such asLentinus tigrinus; Penicillium, such as Penicillium glaucum; Polyporus,such as Polyporus versicolor; Aureobasidium, such as Aureobasidiumpullulans; Sclerophoma, such as Sclerophoma pityophila; Trichoderma,such as Trichoderma virile; Ophiostoma spp., Ceratocystis spp., Humicolaspp., Petriella spp., Trichurus spp., Coriolus spp., Gloeophyllum spp.,Pleurotus spp., Poria spp., Serpula spp. and Tyromyces spp.,Cladosporium spp., Paecilomyces spp. Mucor spp., Escherichia, such asEscherichia coli; Pseudomonas, such as Pseudomonas aeruginosa;Staphylococcus, such as Staphylococcus aureus, Candida spp. andSaccharomyces spp., such as Saccharomyces cerevisae.

Antimycotic Activity

In addition, the inventive active compound combinations also have verygood antimycotic activity. They have a very broad antimycotic activityspectrum, especially against dermatophytes and yeasts, moulds anddiphasic fungi (for example against Candida species, such as C.albicans, C. glabrata), and Epidermophyton floccosum, Aspergillusspecies, such as A. niger and A. fumigatus, Trichophyton species, suchas T. mentagrophytes, Microsporon species such as M. canis and M.audouinii. The list of these fungi by no means constitutes a restrictionof the mycotic spectrum covered, and is merely of illustrativecharacter.

The inventive active compound combinations can therefore be used both inmedical and in non-medical applications

Genetically Modified Organisms

As already mentioned above, it is possible to treat all plants and theirparts in accordance with the invention. In a preferred embodiment, wildplant species and plant cultivars, or those obtained by conventionalbiological breeding methods, such as crossing or protoplast fusion, andalso parts thereof, are treated. In a further preferred embodiment,transgenic plants and plant cultivars obtained by genetic engineeringmethods, if appropriate in combination with conventional methods(Genetically Modified Organisms), and parts thereof are treated. Theterms “plants” or “plant parts” have been explained above. Morepreferably, plants of the plant cultivars which are commerciallyavailable or are in use are treated in accordance with the invention.Plant cultivars are understood to mean plants which have new properties(“traits”) and have been obtained by conventional breeding, bymutagenesis or by recombinant DNA techniques. They can be cultivars,varieties, bio- or genotypes.

The method of treatment according to the invention can be used in thetreatment of genetically modified organisms (GMOs), e.g. plants orseeds. Genetically modified plants (or transgenic plants) are plants ofwhich a heterologous gene has been stably integrated into genome. Theexpression “heterologous gene” essentially means a gene which isprovided or assembled outside the plant and when introduced in thenuclear, chloroplastic or mitochondrial genome gives the transformedplant new or improved agronomic or other properties by expressing aprotein or polypeptide of interest or by downregulating or silencingother gene(s) which are present in the plant (using for example,antisense technology, cosuppression technology, RNAinterference—RNAi-technology or microRNA—miRNA-technology). Aheterologous gene that is located in the genome is also called atransgene. A transgene that is defined by its particular location in theplant genome is called a transformation or transgenic event.

Depending on the plant species or plant cultivars, their location andgrowth conditions (soils, climate, vegetation period, diet), thetreatment according to the invention may also result in superadditive(“synergistic”) effects. Thus, for example, reduced application ratesand/or a widening of the activity spectrum and/or an increase in theactivity of the active compound combinations and compositions which canbe used according to the invention, better plant growth, increasedtolerance to high or low temperatures, increased tolerance to drought orto water or soil salt content, increased flowering performance, easierharvesting, accelerated maturation, higher harvest yields, biggerfruits, larger plant height, greener leaf color, earlier flowering,higher quality and/or a higher nutritional value of the harvestedproducts, higher sugar concentration within the fruits, better storagestability and/or processability of the harvested products are possible,which exceed the effects which were actually to be expected.

The active compound combinations or compositions according to theinvention also have a strengthening effect in plants. Accordingly, theyare also suitable for mobilizing the defense system of the plant againstattack by harmful microorganisms. This may, if appropriate, be one ofthe reasons of the enhanced activity of the active compound combinationsor compositions according to the invention. Plant-strengthening(resistance-inducing) substances are to be understood as meaning, in thepresent context, those substances or combinations of substances whichare capable of stimulating the defense system of plants in such a waythat, when subsequently inoculated with harmful microorganisms, thetreated plants display a substantial degree of resistance to thesemicroorganisms. In the present case, harmful microorganisms are to beunderstood as meaning phytopathogenic fungi. Thus, the substancesaccording to the invention can be employed for protecting plants againstattack by the abovementioned pathogens within a certain period of timeafter the treatment. The period of time within which protection iseffected generally extends from 1 to 10 days, preferably 1 to 7 days,after the treatment of the plants with the active compound combinationor composition.

Plants and plant cultivars which are preferably to be treated accordingto the invention include all plants which have genetic material whichimpart particularly advantageous, useful traits to these plants (whetherobtained by breeding and/or biotechnological means).

Plants and plant cultivars which are also preferably to be treatedaccording to the invention are resistant against one or more bioticstresses, i.e. said plants show a better defense against animal andmicrobial pests, such as against nematodes, insects, mites,phytopathogenic fungi, bacteria, viruses and/or viroids.

Examples of nematode or insect resistant plants are for example thosementioned in WO 2012/045798 A1 and WO 2012/089757 A1.

Plants and plant cultivars which may also be treated according to theinvention are those plants which are resistant to one or more abioticstresses. Abiotic stress conditions may include, for example, drought,cold temperature exposure, heat exposure, osmotic stress, flooding,increased soil salinity, increased mineral exposure, ozone exposure,high light exposure, limited availability of nitrogen nutrients, limitedavailability of phosphorus nutrients, shade avoidance.

Plants and plant cultivars which may also be treated according to theinvention, are those plants characterized by enhanced yieldcharacteristics. Increased yield in said plants can be the result of,for example, improved plant physiology, growth and development, such aswater use efficiency, water retention efficiency, improved nitrogen use,enhanced carbon assimilation, improved photosynthesis, increasedgermination efficiency and accelerated maturation. Yield can furthermorebe affected by improved plant architecture (under stress and non-stressconditions), including but not limited to, early flowering, floweringcontrol for hybrid seed production, seedling vigor, plant size,internode number and distance, root growth, seed size, fruit size, podsize, pod or ear number, seed number per pod or ear, seed mass, enhancedseed filling, reduced seed dispersal, reduced pod dehiscence and lodgingresistance. Further yield traits include seed composition, such ascarbohydrate content, protein content, oil content and composition,nutritional value, reduction in anti-nutritional compounds, improvedprocessability and better storage stability.

Plants that may be treated according to the invention are hybrid plantsthat already express the characteristic of heterosis or hybrid vigorwhich results in generally higher yield, vigor, health and resistancetowards biotic and abiotic stresses). Such plants are typically made bycrossing an inbred male-sterile parent line (the female parent) withanother inbred male-fertile parent line (the male parent). Hybrid seedis typically harvested from the male sterile plants and sold to growers.Male sterile plants can sometimes (e.g. in corn) be produced bydetasseling, i.e. the mechanical removal of the male reproductive organs(or males flowers) but, more typically, male sterility is the result ofgenetic determinants in the plant genome. In that case, and especiallywhen seed is the desired product to be harvested from the hybrid plantsit is typically useful to ensure that male fertility in the hybridplants is fully restored. This can be accomplished by ensuring that themale parents have appropriate fertility restorer genes which are capableof restoring the male fertility in hybrid plants that contain thegenetic determinants responsible for male-sterility. Geneticdeterminants for male sterility may be located in the cytoplasm.Examples of cytoplasmic male sterility (CMS) were for instance describedin Brassica species (WO 92/05251, WO 95/09910, WO 98/27806, WO2005/002324, WO 2006/021972 and U.S. Pat. No. 6,229,072). However,genetic determinants for male sterility can also be located in thenuclear genome. Male sterile plants can also be obtained by plantbiotechnology methods such as genetic engineering. A particularly usefulmeans of obtaining male-sterile plants is described in WO 89/10396 inwhich, for example, a ribonuclease such as barnase is selectivelyexpressed in the tapetum cells in the stamens. Fertility can then berestored by expression in the tapetum cells of a ribonuclease inhibitorsuch as barstar (e.g. WO 91/02069).

Plants or plant cultivars (obtained by plant biotechnology methods suchas genetic engineering) which may be treated according to the inventionare herbicide-tolerant plants, i.e. plants made tolerant to one or moregiven herbicides. Such plants can be obtained either by genetictransformation, or by selection of plants containing a mutationimparting such herbicide tolerance.

Herbicide-resistant plants are for example glyphosate-tolerant plants,i.e. plants made tolerant to the herbicide glyphosate or salts thereof.Plants can be made tolerant to glyphosate through different means, forexample those mentioned in WO 2012/045798 A1 and WO 2012/089757 A1.

Other herbicide resistant plants are for example plants that are madetolerant to herbicides inhibiting the enzyme glutamine synthase, such asbialaphos, phosphinothricin or glufosinate. Such plants can be obtainedfor example by methods mentioned in WO 2012/045798 A1 and WO 2012/089757A1.

Further herbicide-tolerant plants are also plants that are made tolerantto the herbicides inhibiting the enzyme hydroxyphenylpyruvatedioxygenase(HPPD). HPPD is an enzyme that catalyze the reaction in whichpara-hydroxyphenylpyruvate (HPP) is transformed into homogentisate.Plants tolerant to HPPD-inhibitors can be transformed with a geneencoding a naturally-occurring resistant HPPD enzyme, or a gene encodinga mutated or chimeric HPPD enzyme, for example as mentioned in WO2012/045798 A1 and WO 2012/089757 A1.

Still further herbicide resistant plants are plants that are madetolerant to acetolactate synthase (ALS) inhibitors. Known ALS-inhibitorsinclude, for example, sulfonylurea, imidazolinone, triazolopyrimidines,pryimidinyoxy(thio)benzoates, and/or sulfonylaminocarbonyltriazolinoneherbicides. Different mutations in the ALS enzyme (also known asacetohydroxyacid synthase, AHAS) are known to confer tolerance todifferent herbicides and groups of herbicides (see the correspondingreferences mentioned in WO 2012/045798 A1 and WO 2012/089757 A1.

Plants or plant cultivars (obtained by plant biotechnology methods suchas genetic engineering) which may also be treated according to theinvention are insect-resistant transgenic plants, i.e. plants maderesistant to attack by certain target insects. Such plants can beobtained by genetic transformation, or by selection of plants containinga mutation imparting such insect resistance.

An “insect-resistant transgenic plant”, as used herein, in particularrelates to the insect-resistant transgenic plants mentioned in WO2012/045798 A1 and WO 2012/089757 A1.

Plants or plant cultivars (obtained by plant biotechnology methods suchas genetic engineering) which may also be treated according to theinvention are tolerant to abiotic stresses. Such plants can be obtainedby genetic transformation, or by selection of plants containing amutation imparting such stress resistance. Particularly useful stresstolerance plants are those mentioned in WO 2012/045798 A1 and WO2012/089757 A1.

Plants or plant cultivars (obtained by plant biotechnology methods suchas genetic engineering) which may also be treated according to theinvention show altered quantity, quality and/or storage-stability of theharvested product and/or altered properties of specific ingredients ofthe harvested product such those from transgenic plants mentioned in WO2012/045798 A1 and WO 2012/089757 A1.

Plants or plant cultivars (that can be obtained by plant biotechnologymethods such as genetic engineering) which may also be treated accordingto the invention are plants, such as oilseed rape or related Brassicaplants, with altered oil profile characteristics. Such plants can beobtained by genetic transformation, or by selection of plants contain amutation imparting such altered oil profile characteristics and includethe oilseed rape plants mentioned in WO 2012/045798 A1 and WO2012/089757 A1.

Particularly useful transgenic plants which may be treated according tothe invention are plants containing transformation events, orcombination of transformation events, that are the subject of petitionsfor non-regulated status, in the United States of America, to the Animaland Plant Health Inspection Service (APHIS) of the United StatesDepartment of Agriculture (USDA) whether such petitions are granted orare still pending.

Particularly useful transgenic plants which may be treated according tothe invention are plants containing transformation events, or acombination of transformation events, are those mentioned in WO2012/045798 A1 and WO 2012/089757 A1.

Application Rates and Timing

The compounds of the formula (I) and the compounds (II) and (III) of theactive compound combination or composition according to the presentinvention can be combined in any specific ratio between these threemandatory components.

In the active compound combinations or compositions according to theinvention the compounds (I) and (II) or the compounds (I) and (III) orthe compounds (II) and (III) are present in a synergistically effectiveweight ratio of I:II or I:III or II:III in a range of 100:1 to 1:100,preferably in a weight ratio of 50:1 to 1:50, most preferably in aweight ratio of 30:1 to 1:30.

In preferred embodiments of the invention the weight ratio of I:II isfrom 1:1 to 1:20, preferably from 1:1 to 1:10, more preferably from 1:1to 1:5, most preferably from 1:1 to 1:2.

In preferred embodiments of the invention the weight ratio of I:III isfrom 1:1 to 1:10, preferably from 1:1 to 1:5, more preferably from 1:1to 1:2.

In preferred embodiments of the invention the weight ratio of II:III isfrom 20:1 to 1:20, preferably from 10:1 to 1:10, more preferably from5:1 to 1:5, most preferably from 2:1 to 1:2.

In preferred embodiments of the invention the weight ratio of I:II isfrom 1:1 to 1:20 and the weight ratio of I:III is from 1:1 to 1:10,preferably the weight ratio of I:II is from 1:1 to 1:10 and the weightratio of I:III is from 1:1 to 1:5, more preferably the weight ratio ofI:II is from 1:1 to 1:5 and the weight ratio of I:III is from 1:1 to1:2, most preferably the weight ratio of I:II is from 1:1 to 1:2 and theweight ratio of I:III is from 1:1 to 1:2.

In preferred embodiments of the invention the weight ratio of I:II isfrom 1:1 to 1:20 and the weight ratio of II:III is from 20:1 to 1:20,preferably the weight ratio of I:II is from 1:1 to 1:10 and the weightratio of II:III is from 10:1 to 1:10, more preferably the weight ratioof I:II is from 1:1 to 1:5 and the weight ratio of II:III is from 5:1 to1:5, most preferably the weight ratio of I:II is from 1:1 to 1:2 and theweight ratio of II:III is from 2:1 to 1:2.

In preferred embodiments of the invention the weight ratio of I:III isfrom 1:1 to 1:10 and the weight ratio of II:III is from 20:1 to 1:20,preferably the weight ratio of I:III is from 1:1 to 1:5 and the weightratio of II:III is from 10:1 to 1:10, more preferably the weight ratioof I:III is from 1:1 to 1:2 and the weight ratio of II:III is from 5:1to 1:5, most preferably the weight ratio of I:III is from 1:1 to 1:2 andthe weight ratio of II:III is from 2:1 to 1:2.

In preferred embodiments of the invention the weight ratio of I:II isfrom 1:1 to 1:20, the weight ratio of I:III is from 1:1 to 1:10 and theweight ratio of II:III is from 20:1 to 1:20, preferably the weight ratioof I:II is from 1:1 to 1:10, the weight ratio of I:III is from 1:1 to1:5 and the weight ratio of II:III is from 10:1 to 1:10, more preferablythe weight ratio of I:II is from 1:1 to 1:5, the weight ratio of I:IIIis from 1:1 to 1:2 and the weight ratio of II:III is from 5:1 to 1:5,most preferably the weight ratio of I:II is from 1:1 to 1:2, the weightratio of I:III is from 1:1 to 1:2 and the weight ratio of II:III is from2:1 to 1:2.

When using the inventive active compound combinations or compositions asfungicides, the application rates can be varied within a relatively widerange, depending on the kind of application. The application rate of theinventive active compound combinations or compositions is

-   -   in the case of treatment of plants or plant parts, for example        leaves: from 0.1 to 10 000 g/ha, preferably from 10 to 1000        g/ha, more preferably from 10 to 800 g/ha, even more preferably        from 50 to 300 g/ha (in the case of application by watering or        dripping, it is even possible to reduce the application rate,        especially when inert substrates such as rockwool or perlite are        used);    -   in the case of seed treatment: from 2 to 200 g per 100 kg of        seed,    -   in the case of soil treatment: from 0.1 to 10 000 g/ha,        preferably from 1 to 5000 g/ha.

These application rates are merely by way of example and are notlimiting for the purposes of the invention.

The inventive active compound combinations or compositions can thus beused to protect plants from attack by the pathogens mentioned above fora certain period of time after treatment. The period for whichprotection is provided extends generally for 1 to 28 days, preferablyfor 1 to 14 days, more preferably for 1 to 10 days, most preferably for1 to 7 days, after the treatment of the plants with the active compoundcombinations, or for up to 200 days after a seed treatment.

The method of treatment according to the invention also provides the useor application of compounds (I) and (II) and (III) in a simultaneous,separate or sequential manner. If the single active ingredients areapplied in a sequential manner, i.e. at different times, they areapplied one after the other within a reasonably short period, such as afew hours or days. Preferably the order of applying the compounds (I)and (II) and (III) is not essential for working the present invention.

The plants listed above can particularly advantageously be treated inaccordance with the invention with the active compound combinations orcompositions. The preferred ranges stated above for the active compoundcombinations or compositions also apply to the treatment of theseplants. Particular emphasis is given to the treatment of plants with theactive compound combinations or compositions specifically mentioned inthe present description. As mentioned above the mixing ratio ispreferably to be chosen such that a synergistic active compoundcombination is obtained. A synergistic effect of fungicides is alwayspresent when the fungicidal activity of the active compound combinationsexceeds the total of the activities of the active compounds when appliedindividually. The expected activity for a given combination of twoactive compounds can be calculated as follows (cf. Colby, S. R.,“Calculating Synergistic and Antagonistic Responses of HerbicideCombinations”, Weeds 1967, 15, 20-22):

If

-   -   X is the efficacy when active compound (I) is applied at an        application rate of m ppm (or g/ha),    -   Y is the efficacy when active compound (II) is applied at an        application rate of n ppm (or g/ha),    -   Z is the efficacy when active compound (III) is applied at an        application rate of r ppm (or g/ha),    -   E₁ is the efficacy when the active compounds (I) and (II) are        applied at application rates of m and n ppm (or g/ha),        respectively, and    -   E₂ is the efficacy when the active compounds (I), (II) and (III)        are applied at application rates of m, n and r ppm (or g/ha),        respectively, and        then

$E_{1} = {X + Y - \frac{X \cdot Y}{100}}$and for a ternary active compound combination:

$E_{2} = {X + Y + Z - \left( \frac{{X \cdot Y} + {X \cdot Z} + {Y \cdot Z}}{100} \right) + \frac{X \cdot Y \cdot Z}{10000}}$

The degree of efficacy, expressed in % is denoted. 0% means an efficacywhich corresponds to that of the control while an efficacy of 100% meansthat no disease is observed.

If the actual fungicidal activity exceeds the calculated value, then theactivity of the active compound combination is superadditive, i.e. asynergistic effect exists. In this case, the efficacy which was actuallyobserved must be greater than the value for the expected efficacy (E)calculated from the abovementioned formula.

A further way of demonstrating a synergistic effect is the method ofTammes (cf. “Isoboles, a graphic representation of synergism inpesticides” in Neth. J. Plant Path., 1964, 70, 73-80).

The invention is illustrated by the following examples. However theinvention is not limited to the examples.

Example A: In Vivo Preventive Test on Alternaria Test (Tomatoes)

Solvent: 24.5 parts by weight of acetone 24.5 parts by weight ofdimethylacetamide Emulsifier: 1 part by weight of alkylaryl polyglycolether

To produce a suitable preparation of active compound, 1 part by weightof active compound is mixed with the stated amounts of solvent andemulsifier, and the concentrate is diluted with water to the desiredconcentration.

To test for preventive activity, young plants are sprayed with thepreparation of active compound at the stated rate of application. Afterthe spray coating has dried on, the plants are inoculated with anaqueous spore suspension of Alternaria solani. The plants are thenplaced in an incubation cabinet at approximately 20° C. and a relativeatmospheric humidity of 100%.

The test is evaluated 3 days after the inoculation. 0% means an efficacywhich corresponds to that of the untreated control while an efficacy of100% means that no disease is observed. The table below clearly showsthat the observed activity of the active compound combination accordingto the invention is greater than the calculated activity, i.e. asynergistic effect is present.

TABLE A1 in vivo preventive test on Alternaria test (tomatoes)Application rate of active compound in Efficacy in % Active compoundsppm a.i. found* calc.** diff.*** (I-d)N′-(2,5-dimethyl-4-phenoxyphenyl)-N- 1 15 ethyl-N-methylimidoformamide0.5 8 (A.4) tebuconazole 1 0 (B.1) bixafen 1 40 (C.4) trifloxystrobin 130 (B.8) N-(5-chloro-2-isopropylbenzyl)-N- 1 45cyclopropyl-3-(difluoromethyl)-5- fluoro-1-methyl-1H-pyrazole-4-carboxamide (I-d) + (A.4) + (B.1) 1:1:1 1 + 1 + 1 73 49 24 (I-d) +(A.4) + (C.4) 1:1:1 1 + 1 + 1 60 41 19 (I-d) + (A.4) + (B.8) 1:2:2 0.5 +1 + 1   65 49 16 *found = activity found **calc. = activity calculatedusing Colby's formula ***diff. = difference between activity found andactivity calculated

TABLE A2 in vivo preventive test on Alternaria test (tomatoes)Application rate of active compound in Efficacy in % Active compoundsppm a.i. found* calc.** diff*** (I-d)N′-(2,5-dimethyl-4-phenoxyphenyl)-N- 0.2 0 ethyl-N-methylimidoformamide0.1 0 (A.3) prothioconazole 4 24 2 0 (B.2) fluopyram 2 30 (B.6)benzovindiflupyr 0.5 22 (C.1) azoxystrobin 1 46 (C.4) trifloxystrobin 473 (I-d) + (A.3) + (B.2) 1:20:20 0.1 + 2 + 2 88 30 58 (I-d) + (A.3) +(B.6) 1:20:5   0.1 + 2 + 0.5 78 22 56 (I-d) + (A.3) + (C.1) 1:20:100.1 + 2 + 1 95 46 49 (I-d) + (A.3) + (C.4) 1:20:20 0.2 + 4 + 4 88 79 9*found = activity found **calc. = activity calculated using Colby'sformula ***diff. = difference between activity found and activitycalculated

Example B: In Vivo Preventive Blumeria Test (Barley)

Solvent: 49 parts by weight of N,N-dimethylacetamide Emulsifier: 1 partby weight of alkylaryl polyglycol ether

To produce a suitable preparation of active compound, 1 part by weightof active compound or active compound combination is mixed with thestated amounts of solvent and emulsifier, and the concentrate is dilutedwith water to the desired concentration.

To test for preventive activity, young plants are sprayed with thepreparation of active compound or active compound combination at thestated rate of application. After the spray coating has been dried, theplants are dusted with spores of Blumeria graminis f.sp. hordei. Theplants are placed in the greenhouse at a temperature of approximately18° C. and a relative atmospheric humidity of approximately 80% topromote the development of mildew pustules.

The test is evaluated 7 days after the inoculation. 0% means an efficacywhich corresponds to that of the untreated control, while an efficacy of100% means that no disease is observed. The table below clearly showsthat the observed activity of the active compound combination accordingto the invention is greater than the calculated activity, i.e. asynergistic effect is present.

TABLE B1 in vivo preventive Blumeria test (barley) Application rate ofactive compound in Efficacy in % Active compounds ppm a.i. found*calc.** diff.*** (I-d) N′-(2,5-dimethyl-4-phenoxyphenyl)-N- 40 33ethyl-N-methylimidoformamide (B.6) benzovindiflupyr 40 11 (C.2)picoxystrobin 20 44 (I-d) + (A.3) + (C.2) 2:2:1 40 + 40 + 20 78 67 11*found = activity found **calc. = activity calculated using Colby'sformula ***diff. = difference between activity found and activitycalculated

TABLE B2 in vivo preventive Blumeria test (barley) Application rate ofactive compound in Efficacy in % Active compounds ppm a.i. found*calc.** diff.*** (I-d) N′-(2,5-dimethyl-4-phenoxyphenyl)-N- 80 22ethyl-N-methylimidoformamide 40 0 20 0 10 0 (A.3) prothioconazole 40 2210 22 (B.1) bixafen 40 0 (B.2) fluopyram 40 11 (C.4) trifloxystrobin 1011 (I-d) + (A.3) + (B.1) 2:1:1 80 + 40 + 40 100 39 61 (I-d) + (A.3) +(B.1) 1:1:1 40 + 40 + 40 78 22 56 (I-d) + (A.3) + (B.2) 2:1:1 80 + 40 +40 89 46 43 (I-d) + (A.3) + (B.2) 1:1:1 40 + 40 + 40 89 31 58 (I-d) +(A.3) + (C.4) 2:1:1 20 + 10 + 10 44 31 13 (I-d) + (A.3) + (C.4) 1:1:110 + 10 + 10 67 31 36 *found = activity found **calc. = activitycalculated using Colby's formula ***diff. = difference between activityfound and activity calculated

Example C: In Vivo Preventive Leptosphaeria nodorum Test (Wheat)

Solvent: 49 parts by weight of N,N-dimethylacetamide Emulsifier: 1 partby weight of alkylaryl polyglycol ether

To produce a suitable preparation of active compound, 1 part by weightof active compound or active compound combination is mixed with thestated amounts of solvent and emulsifier, and the concentrate is dilutedwith water to the desired concentration.

To test for preventive activity, young plants are sprayed with thepreparation of active compound or active compound combination at thestated rate of application. After the spray coating has been dried, theplants are sprayed with a spore suspension of Leptosphaeria nodorum. Theplants remain for 48 hours in an incubation cabinet at approximately 20°C. and a relative atmospheric humidity of approximately 100%. The plantsare placed in the greenhouse at a temperature of approximately 25° C.and a relative atmospheric humidity of approximately 80%.

The test is evaluated 8 days after the inoculation. 0% means an efficacywhich corresponds to that of the untreated control, while an efficacy of100% means that no disease is observed. The table below clearly showsthat the observed activity of the active compound combination accordingto the invention is greater than the calculated activity, i.e. asynergistic effect is present.

TABLE C1 in vivo preventive Leptosphaeria nodorum test (wheat)Application rate of active compound in Efficacy in % Active compoundsppm a.i. found* calc.** diff.*** (I-d)N′-(2,5-dimethyl-4-phenoxyphenyl)-N- 80 29 ethyl-N-methylimidoformamide(B.1) bixafen 80 0 (B.3) fluxapyroxad 40 14 (B.8)N-(5-chloro-2-isopropylbenzyl)-N- 20 0 cyclopropyl-3-(difluoromethyl)-5-fluoro-1-methyl-1H-pyrazole-4- carboxamide (C.3) pyraclostrobin 40 57(C.4) trifloxystrobin 40 14 (I-d) + (B.1) + (C.4) 2:2:1 80 + 80 + 40 7139 32 (I-d) + (B.3) + (C.3) 2:1:1 80 + 40 + 40 86 74 12 (I-d) + (B.8) +(C.4) 2:0.5:1 80 + 20 + 40 71 39 32 *found = activity found **calc. =activity calculated using Colby's formula ***diff. = difference betweenactivity found and activity calculated

Example D: In Vivo Preventive Test on Phakopsora Test (Soybeans)

Solvent: 24.5 parts by weight of acetone 24.5 parts by weight ofdimethylacetamide Emulsifier: 1 part by weight of alkylaryl polyglycolether

To produce a suitable preparation of active compound, 1 part by weightof active compound is mixed with the stated amounts of solvent andemulsifier, and the concentrate is diluted with water to the desiredconcentration. To test for preventive activity, young plants are sprayedwith the preparation of active compound at the stated rate ofapplication. After the spray coating has dried on, the plants areinoculated with an aqueous spore suspension of the causal agent ofsoybean rust (Phakopsora pachyrhizi) and stay for 24 h without light inan incubation cabinet at approximately 24° C. and a relative atmospherichumidity of 95%. The plants remain in the incubation cabinet atapproximately 24° C. and a relative atmospheric humidity ofapproximately 80% and a day/night interval of 12 h.

The test is evaluated 7 days after the inoculation. 0% means an efficacywhich corresponds to that of the untreated control, while an efficacy of100% means that no disease is observed. The table below clearly showsthat the observed activity of the active compound combination accordingto the invention is greater than the calculated activity, i.e. asynergistic effect is present.

TABLE D1 in vivo preventive test on Phakopsora test (soybeans)Application rate of active compound in Efficacy in % Active compoundsppm a.i. found* calc.** diff.*** (I-d)N′-(2,5-dimethyl-4-phenoxyphenyl)-N- 0.2 86 ethyl-N-methylimidoformamide0.1 23 0.05 0 (A.4) tebuconazole 0.2 30 0.1 0 (B.1) bixafen 10 0 (B.8)N-(5-chloro-2-isopropylbenzyl)-N- 20 0 cyclopropyl-3-(difluoromethyl)-5-fluoro-1-methyl-1H-pyrazole-4- carboxamide (I-d) + (A.4) + (B.1) 1:1:1000.1 + 0.1 + 10 73 23 50 (I-d) + (A.4) + (B.1) 1:2:200 0.05 + 0.1 + 10 60 0 60 (I-d) + (A.4) + (B.8) 1:1:100 0.2 + 0.2 + 20 99 90 9 (I-d) +(A.4) + (B.8) 1:2:200 0.1 + 0.2 + 20 84 46 38 *found = activity found**calc. = activity calculated using Colby's formula ***diff. =difference between activity found and activity calculated

TABLE D2 in vivo preventive test on Phakopsora test (soybeans)Application rate of active compound in Efficacy in % Active compoundsppm a.i. found* calc.** diff.*** (I-d)N′-(2,5-dimethyl-4-phenoxyphenyl)-N- 0.2 23 ethyl-N-methylimidoformamide0.1 0 0.05 0 (B.6) benzovindiflupyr 1 15 0.5 8 0.25 8 (C.1) azoxystrobin1 68 0.5 20 (C.2) picoxystrobin 2 30 (I-d) + (B.6) + (C.1) 1:5:10 0.1 +0.5 + 1 94 71 23 (I-d) + (B.6) + (C.1) 1:5:10 0.05 + 0.25 + 0.5 78 26 52(I-d) + (B.6) + (C.2) 1:5:10 0.2 + 1 + 2 83 54 29 *found = activityfound **calc. = activity calculated using Colby's formula ***diff. =difference between activity found and activity calculated

TABLE D3 in vivo preventive test on Phakopsora test (soybeans)Application rate of active compound in Efficacy in % Active compoundsppm a.i. found* calc.** diff.*** (I-d)N′-(2,5-dimethyl-4-phenoxyphenyl)-N- 0.1 0 ethyl-N-methylimidoformamide0.05 0 (A.3) prothioconazole 2 35 1 0 (B.1) bixafen 10 0 (B.8)N-(5-chloro-2-isopropylbenzyl)-N- 10 0 cyclopropyl-3-(difluoromethyl)-5-fluoro-1-methyl-1H-pyrazole-4- carboxamide (C.1) azoxystrobin 0.5 23(C.4) trifloxystrobin 2 0 (I-d) + (A.3) + (B.1) 1:20:100 0.1 + 2 + 10 6535 30 (I-d) + (A.3) + (B.8) 1:20:100 0.1 + 2 + 10 80 35 45 (I-d) +(A.3) + (C.1) 1:20:10 0.05 + 1 + 0.5  78 23 55 (I-d) + (A.3) + (C.4)1:20:20 0.1 + 2 + 2  58 35 23 *found = activity found **calc. = activitycalculated using Colby's formula ***diff. = difference between activityfound and activity calculated

Example E: In Vivo Preventive Puccinia triticina Test (Wheat)

Solvent: 49 parts by weight of N,N-dimethylacetamide Emulsifier: 1 partby weight of alkylaryl polyglycol ether

To produce a suitable preparation of active compound, 1 part by weightof active compound or active compound combination is mixed with thestated amounts of solvent and emulsifier, and the concentrate is dilutedwith water to the desired concentration.

To test for preventive activity, young plants are sprayed with thepreparation of active compound or active compound combination at thestated rate of application. After the spray coating has been dried, theplants are sprayed with a spore suspension of Puccinia triticina. Theplants remain for 48 hours in an incubation cabinet at approximately 20°C. and a relative atmospheric humidity of approximately 100%. The plantsare placed in the greenhouse at a temperature of approximately 20° C.and a relative atmospheric humidity of approximately 80%.

The test is evaluated 8 days after the inoculation. 0% means an efficacywhich corresponds to that of the untreated control, while an efficacy of100% means that no disease is observed. The table below clearly showsthat the observed activity of the active compound combination accordingto the invention is greater than the calculated activity, i.e. asynergistic effect is present.

TABLE E1 in vivo preventive Puccinia triticina test (wheat) Applicationrate of active compound in Efficacy in % Active compounds ppm a.i.found* calc.** diff.*** (I-d) N′-(2,5-dimethyl-4-phenoxyphenyl)-N- 40 57ethyl-N-methylimidoformamide (B.6) benzovindiflupyr 40 86 (C.1)azoxystrobin 10 71 (I-d) + (B.6) + (C.1) 4:4:1 40 + 40 + 10 100 98 2*found = activity found **calc. = activity calculated using Colby'sformula ***diff. = difference between activity found and activitycalculated

Example F: In Vivo Preventive Pyrenophora teres Test (Barley)

Solvent: 49 parts by weight of N,N-dimethylacetamide Emulsifier: 1 partby weight of alkylaryl polyglycol ether

To produce a suitable preparation of active compound, 1 part by weightof active compound or active compound combination is mixed with thestated amounts of solvent and emulsifier, and the concentrate is dilutedwith water to the desired concentration.

To test for preventive activity, young plants are sprayed with thepreparation of active compound or active compound combination at thestated rate of application. After the spray coating has been dried, theplants are sprayed with a spore suspension of Pyrenophora teres. Theplants remain for 48 hours in an incubation cabinet at approximately 20°C. and a relative atmospheric humidity of approximately 100%. The plantsare placed in the greenhouse at a temperature of approximately 20° C.and a relative atmospheric humidity of approximately 80%.

The test is evaluated 8 days after the inoculation. 0% means an efficacywhich corresponds to that of the untreated control, while an efficacy of100% means that no disease is observed. The table below clearly showsthat the observed activity of the active compound combination accordingto the invention is greater than the calculated activity, i.e. asynergistic effect is present.

TABLE F1 in vivo preventive Pyrenophora teres test (barley) Applicationrate of active compound in Efficacy in % Active compounds ppm a.i.found* calc.** diff.*** (I-d) N′-(2,5-dimethyl-4-phenoxyphenyl)-N- 80 29ethyl-N-methylimidoformamide (B.6) benzovindiflupyr 80 57 (C.1)azoxystrobin 20 71 (I-d) + (B.6) + (C.1) 4:4:1 80 + 80 + 20 100 91 9*found = activity found **calc. = activity calculated using Colby'sformula ***diff. = difference between activity found and activitycalculated

Example G: In Vivo Preventive Septoria tritici Test (Wheat)

Solvent: 49 parts by weight of N,N-dimethylacetamide Emulsifier: 1 partby weight of alkylaryl polyglycol ether

To produce a suitable preparation of active compound, 1 part by weightof active compound or active compound combination is mixed with thestated amounts of solvent and emulsifier, and the concentrate is dilutedwith water to the desired concentration.

To test for preventive activity, young plants are sprayed with thepreparation of active compound or active compound combination at thestated rate of application. After the spray coating has been dried, theplants are sprayed with a spore suspension of Septoria tritici. Theplants remain for 48 hours in an incubation cabinet at approximately 20°C. and a relative atmospheric humidity of approximately 100% andafterwards for 60 hours at approximately 15° C. in a translucentincubation cabinet at a relative atmospheric humidity of approximately100%. The plants are placed in the greenhouse at a temperature ofapproximately 15° C. and a relative atmospheric humidity ofapproximately 80%.

The test is evaluated 21 days after the inoculation. 0% means anefficacy which corresponds to that of the untreated control, while anefficacy of 100% means that no disease is observed. The table belowclearly shows that the observed activity of the active compoundcombination according to the invention is greater than the calculatedactivity, i.e. a synergistic effect is present.

TABLE G1 in vivo preventive Septoria tritici test (wheat) Applicationrate of active compound in Efficacy in % Active compounds ppm a.i.found* calc.** diff.*** (I-d) N′-(2,5-dimethyl-4-phenoxyphenyl)-N- 40 14ethyl-N-methylimidoformamide 20 14 (A.3) prothioconazole 20 0 (B.8)N-(5-chloro-2-isopropylbenzyl)-N- 20 29cyclopropyl-3-(difluoromethyl)-5- fluoro-1-methyl-1H-pyrazole-4-carboxamide (I-d) + (A.3) + (B.8) 2:1:1 40 + 20 + 20 57 39 18 (I-d) +(A.3) + (B.8) 1:1:1 20 + 20 + 20 43 39 4 *found = activity found **calc.= activity calculated using Colby's formula ***diff. = differencebetween activity found and activity calculated

TABLE G2 in vivo preventive Septoria tritici test (wheat) Applicationrate of active compound in Efficacy in % Active compounds ppm a.i.found* calc.** diff.*** (I-d) N′-(2,5-dimethyl-4-phenoxyphenyl)-N- 80 0ethyl-N-methylimidoformamide 40 0 (B.1) bixafen 40 0 (B.3) fluxapyroxad40 13 (B.6) benzovindiflupyr 40 38 (C.1) azoxystrobin 10 0 (C.3)pyraclostrobin 40 88 (C.4) trifloxystrobin 20 75 (I-d) + (B.1) + (C.4)2:1:1 40 + 40 + 20 94 75 19 (I-d) + (B.3) + (C.3) 2:1:1 80 + 40 + 40 9490 4 (I-d) + (B.6) + (C.1) 4:4:1 40 + 40 + 10 50 38 12 *found = activityfound **calc. = activity calculated using Colby's formula ***diff. =difference between activity found and activity calculated

The invention claimed is:
 1. An active compound combination comprising(1) at least one compound of the formula (I)

in which R¹ is selected from the group consisting of methyl and ethyl;R² is selected from the group consisting of a Cl atom and a methylgroup; R³ is selected from the group consisting of a Cl-atom and amethyl group; R⁴ is selected from the group consisting of hydrogen,halogen or methyl; R⁵ is selected from the group consisting of hydrogen,halogen or methyl; and/or a salt, N-oxide, metal complex and/orstereoisomer thereof and (2) at least two compounds (II) and (III)selected from the groups (A), (B) and/or (C): (A) the group ofinhibitors of the ergosterol biosynthesis; (B) the group of inhibitorsof the respiratory chain at complex I or II; and (C) the group ofinhibitors of the respiratory chain at complex III; with the provisothat the specified compounds (II) and (III) are not identical, andwherein the compound of the group (A) of inhibitors of the ergosterolbiosynthesis is selected from the group consisting of (A.1)cyproconazole (113096-99-4), (A.2) epoxiconazole (106325-08-0), (A.3)prothioconazole (178928-70-6) and (A.4) tebuconazole (107534-96-3); andwherein the compound of the group (B) of inhibitors of the respiratorychain at complex I or II is selected from the group consisting of (B.1)bixafen (581809-46-3), (B.2) fluopyram (658066-35-4), (B.3) fluxapyroxad(907204-31-3), (B.4) isopyrazam (mixture of syn-epimeric racemate1RS,4SR,9RS and anti-epimeric racemate 1RS,4SR,9SR) (881685-58-1), (B.5)penthiopyrad (183675-82-3), (B.6) benzovindiflupyr (1072957-71-1), (B.7)isofetamid (875915-78-9), (B.8)N-(5-chloro-2-isopropylbenzyl)-N-cyclopropyl-3-(difluoromethyl)-5-fluoro-1-methyl-1H-pyrazole-4-carboxamideand (B.9)3-(difluoromethyl)-N-methoxy-1-methyl-N-[1-(2,4,6-trichlorophenyl)propan-2-yl]-1H-pyrazole-4-carboxamide,and wherein the compound of the group (C) of inhibitors of therespiratory chain at complex III is selected from the group consistingof (C.1) azoxystrobin (131860-33-8), (C.2) picoxystrobin (117428-22-5),(C.3) pyraclostrobin (175013-18-0) and (C.4) trifloxystrobin(141517-21-7).
 2. An active compound combination according to claim 1,wherein the compound of formula (I) is represented by a compoundaccording to formula (I-d):

and/or a salt, N-oxide, metal complex and/or stereoisomer thereof. 3.The active compound combination according to claim 2, selected from thegroup consisting of (I-d)+benzovindiflupyr+tebuconazole;(I-d)+benzovindiflupyr+cyproconazole;(I-d)+benzovindiflupyr+epoxiconazole; (I-d)+penthiopyrad+cyproconazole;(I-d)+penthiopyrad+epoxiconazole; (I-d)+fluxapyroxad+prothioconazole;(I-d)+fluxapyroxad+tebuconazole; (I-d)+fluxapyroxad+epoxiconazole;(I-d)+isopyrazam+cyproconazole; (I-d)+isopyrazam+epoxiconazole;(I-d)+trifloxystrobin+Benzovindiflupyr;(I-d)+trifloxystrobin+fluxapyroxad; (I-d)+azoxystrobin+tebuconazole;(I-d)+azoxystrobin+cyproconazole; (I-d)+azoxystrobin+epoxiconazole;(I-d)+azoxystrobin+bixafen; (I-d)+azoxystrobin+fluxapyroxad;(I-d)+azoxystrobin+isopyrazam; (I-d)+pyraclostrobin+prothioconazole;(I-d)+pyraclostrobin+tebuconazole; (I-d)+pyraclostrobin+epoxiconazole;(I-d)+pyraclostrobin+bixafen; (I-d)+picoxystrobin+prothioconazole;(I-d)+Picoxystrobin+tebuconazole;(I-d)+N-(5-chloro-2-isopropylbenzyl)-N-cyclopropyl-3-(difluoromethyl)-5-fluoro-1-methyl-1H-pyrazole-4-carboxamide+azoxystrobin;(I-d)+N-(5-chloro-2-isopropylbenzyl)-N-cyclopropyl-3-(difluoromethyl)-5-fluoro-1-methyl-1H-pyrazole-4-carboxamide+pyraclostrobin;(I-d)+3-(difluoromethyl)-N-methoxy-1-methyl-N-[1-(2,4,6-trichlorophenyl)propan-2-yl]-1H-pyrazole-4-carboxamide+tebuconazole;(I-d)+3-(difluoromethyl)-N-methoxy-1-methyl-N-[1-(2,4,6-trichlorophenyl)propan-2-yl]-1H-pyrazole-4-carboxamide+bixafenand(I-d)+3-(difluoromethyl)-N-methoxy-1-methyl-N-[1-(2,4,6-trichlorophenyl)propan-2-yl]-1H-pyrazole-4-carboxamide+benzovindiflupyr.4. The active compound combination according to claim 2, selected fromthe group consisting of (I-d)+fluopyram+tebuconazole;(I-d)+trifloxystrobin+cyproconazole; (I-d)+isofetamid+prothioconazole;(I-d)+isofetamid+tebuconazole; (I-d)+fluopyram+bixafen;(I-d)+trifloxystrobin+fluopyram; (I-d)+isofetamid+bixafen and(I-d)+isofetamid+trifloxystrobin.
 5. The active compound combinationaccording to claim 2, selected from the group consisting of(I-d)+bixafen+prothioconazole; (I-d)+fluopyram+prothioconazole;(I-d)+benzovindiflupyr+prothioconazole;(I-d)+trifloxystrobin+prothioconazole;(I-d)+azoxystrobin+prothioconazole;(I-d)+N-(5-chloro-2-isopropylbenzyl)-N-cyclopropyl-3-(difluoromethyl)-5-fluoro-1-methyl-1H-pyrazole-4-carboxamide+prothioconazole;(I-d)+bixafen+tebuconazole; (I-d)+trifloxystrobin+tebuconazole;(I-d)+N-(5-chloro-2-isopropylbenzyl)-N-cyclopropyl-3-(difluoromethyl)-5-fluoro-1-methyl-1H-pyrazole-4-carboxamide+tebuconazole;(I-d)+trifloxystrobin+bixafen; (I-d)+azoxystrobin+benzovindiflupyr;(I-d)+picoxystrobin+penthiopyrad; (I-d)+picoxystrobin+benzovindiflupyr;(I-d)+pyraclostrobin+fluxapyroxad and(I-d)+N-(5-chloro-2-isopropylbenzyl)-N-cyclopropyl-3-(difluoromethyl)-5-fluoro-1-methyl-1H-pyrazole-4-carboxamide+trifloxystrobin.6. A composition comprising an active compound combination according toclaim
 1. 7. A composition according to claim 6 further comprising atleast one agriculturally suitable additive.
 8. A method for preparing acomposition according to claim 6 comprising adding at least oneagriculturally suitable additive to the active compound combinationaccording to claim
 1. 9. A method for reducing damage of plants andplant parts or losses in harvested fruits or vegetables caused byphytopathogenic fungi by controlling such phytopathogenic fungi,comprising applying the active compound combination according to claim 1to the plant or the phytopathogenic fungi or the habitat of the plant orthe habitat of the phytopathogenic fungi.
 10. A method for curatively orpreventively controlling phytopathogenic fungi comprising application ofan active compound combination according to claim 1 or a compositionthereof for control of one or more soybean diseases.
 11. A method forcuratively or preventively controlling phytopathogenic fungi comprisingapplication of an active compound combination according to claim 1 or acomposition thereof for control of one or more cereal diseases.
 12. Seedtreated with the active compound combination according to claim 1 or acomposition thereof, wherein the treatment comprises-contacting saidseed with the active compound combination.
 13. The method according toclaim 9, wherein the plants are genetically modified.
 14. The activecompound combination according to claim 1, comprising a compound offormula (I) and a compound (II) in a weight ratio of 1:1 to 1:20. 15.The active compound combination according to claim 1, comprising acompound of formula (I) and a compound (III) in a weight ratio of 1:1 to1:10.
 16. The active compound combination according to claim 14,comprising a compound of formula (I) and a compound (III) in a weightratio of 1:1 to 1:10.
 17. The active compound combination according toclaim 1, comprising tebuconazole.
 18. The active compound combinationaccording to claim 1, comprising prothioconazole.